Category: 50866-30-3

Application of 50866-30-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

To the starting material 5-methylpyrazine-2-carbaldehyde (100 mg, 0.8 mmol), THF (1.0mL) was added followed by phosphorene 8 (250 mg 1.7 mmol) at room temperature. Thereaction mixture was stirred for 8 h at 60 C. TLC revealed complete consumption ofstarting material. The reaction mixture was removed from heating bath and quenchedusing a saturated aqueous NH4Cl solution. Water (10 mL) and ethyl acetate (25 mL) wereadded, layers were separated washed with brine solution, dried over sodium sulfate andevaporated under reduced pressure to dryness. Then column purification was done to getthe pure product which was characterized by NMR. Yield: 72%

The chemical industry reduces the impact on the environment during synthesis 5-Methylpyrazine-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Balasubramaniam, Sivaraman; Vijayan, Sajith; Goldman, Liam V.; May, Xavier A.; Dodson, Kyra; Adhikari, Sweta; Rivas, Fatima; Watkins, Davita L.; Stoddard, Shana V.; Beilstein Journal of Organic Chemistry; vol. 16; (2020); p. 628 – 637;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 50866-30-3 as follows. Recommanded Product: 50866-30-3

To a solution of 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (4.4 g) in dimethylformamide (62 mL) was added acetic acid (2.4 mL), 5-methylpyrazine-2-carbaldehyde (2 g) and sodium triacetoxyborohydride (5.27 g). The reaction mixture stirred for 2 h at ambient temperature and was carefully quenched with saturated sodium bicarbonate solution, extracted 3* with methylene chloride, dried with magnesium sulfate, filtered and concentrated. Purification via Biotage MPLC chromatography eluding with 1-4% methanolmethylene chloride/0.5% saturated ammonium hydroxide provided the title compound (3.9 g). 400 MHz 1H NMR (CDCl3) delta 8.52-8.48 (m, 1H), 8.38 (s, 1H), 8.02 (s, 1H), 4.81-4.75 (m, 1H), 4.11-4.01 (m, 3H), 3.79-3.75 (m, 1H), 3.60-3.53 (m, 2H), 3.40-3.32 (m, 1H), 3.10-3.08 (m, 1H), 2.94 (m, 1H), 2.63-2.57 (m, 1H), 2.53 (d, J=7.5 Hz, 1H), 2.37-2.18 (m, 4H), 1.90-1.83 (m, 2H), 1.67-1.60 (m, 1H), 1.54-1.47 (m, 1H), 0.95-0.92 (m, 3H). MS: (M+H m/z 424.2).

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 50866-30-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 50866-30-3 name is 5-Methylpyrazine-2-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[011761 (1R,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin- 2-yl)propane-2-sulfonamide and (1S,2R)- 1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5- methylpyrazin-2-yl)propane-2-sulfonamide and (1 S,2S)-1-hydroxy-N,N-bis(4- methoxybenzyl)- 1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and (1R,2S)-1- hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and Example 564.1. At -78 C, an- butyllithium solution (2.5 M in hexanes, 10.2525.6 mmol) was added to a 2-methyltetrahydrofuran (107 mL) solution containing N,Nbis(4-methoxybenzyl)ethanesulfonamide (7.46 g, 21.36 mmol). The resulting mixture was stirred for 15 mm at -78 C. Next, a 2-methyltetrahydrofuran solution containingmethyl-2-pyrazinecarbaldehyde (2.66 mL, 25.6 mmol) was added at -78 C and thenreaction was allowed to slowly warm to RT and stirred overnight. The reaction was quenched with a saturated ammonium chloride solution and partitioned. The remaining residue was purified on silica eluting with a DCM/EtOAc gradient (0-50%). Desired fractions were then combined and concentrated in vacuo. MS ESI (pos.) mlz: 472.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methylpyrazine-2-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 50866-30-3 as follows. Safety of 5-Methylpyrazine-2-carbaldehyde

b) 6-{(3S.4S)-4-ethyl-1-f(5-methylpyrazin-2-vnmethyllpyrrolidin-3-yl>-1- (tetrahvdro-2H-pyran-4-yl)-1.5-dihvdro-4H-pyrazolof3.4-dipyrimidin-4-oneTo a solution -3-yl]-1-(tetrahydro-2H- pyran-4-yl)-1H-pyrazolo[3,4-d]pynmidin-4(5H)-one (4.4g) in dimethylformamide (62 mL) was added acetic acid (2 4 ml_), 5- methylpyrazine-2-carbaldehyde (2g) and sodium tnacetoxyborohydnde (5 27g) The reaction mixture stirred for 2h at ambient temperature and was carefully quenched with saturated sodium bicarbonate solution, extracted 3x with methylene chloride, dried with magnesium sulfate, filtered and concentrated Purification via Biotage MPLC chromatography eluting with 1 – 4% methanol/methylene chlonde/0 5 % saturated ammonium hydroxide provided the title compound (3 9g) 400 MHz 1H NMR (CDCI3) delta 8 52-8 48 (m, 1 H), 8 38 (s, 1 H), 8 02 (s, 1 H), 4 81-4 75 (m, 1 H), 4 1 1 -4 01 (m, 3H), 3 79-3 75 (m, 1 H) , 3 60-3 53 (m, 2H), 3 40-3 32 (m, 1 H), 3 10-3 08 (m, 1 H), 2 94 (m, 1 H), 2 63-2 57 (m, 1 H), 2 53 (d, J = 7 5 Hz, 1 H), 2 37-2 18 (m, 4H), 1 90-1 83 (m, 2H), 1 67-1 60 (m, 1 H), 1 54-1 47 (m, 1 H), 0 95-0 92 (m, 3H) MS (M+H m/z 424 2)

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2008/139293; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 50866-30-3 as follows.

To a solution of N,Nbis(4-methoxybenzyl)ethanesulfonamide (Example 361.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78C was added n-butyllithium (83.71 mL, 0.21 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 mm. A solution of 5 -methylpyrazine-2-carbaldehyde (Example 376.1, 21.3 g, 0.17 mol, 1.0 equiv.) in anhydrous THF (150 mL) was then added, and the mixture was stirred at the same temperature for 45 mm and then allowed to warm to RT for 2 h. The reaction mixture was quenched by addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo to afford the initial product as an oil. The oil was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g as white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) oe 8.61 (d, J 1.5 Hz, 1H), 8.51 (d, J= 1.5 Hz, 1H), 7.22-7.11 (m, 4H), 6.90-6.80 (m, 4H), 6.10 (d, J 5.9 Hz, 1H), 5.29 (dd, J= 5.9, 2.2 Hz, 1H), 4.36-4.16 (m, 4H), 3.73 (app s, 6H), 3.70-3.66 (m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d, J = 7.0 Hz, 3H). LCMS (ESI positive ion) m/z: 472.4 (M+H)t

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Synthetic Route of 50866-30-3, These common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the BOC-protected intermediate from Example 2 (32 mg, 0.07 mmol) in 1/1 dichloromethane/ methanol (1 mL) was added a solution of 5-methylpyrazine-2-carbaldehyde (11 mg, 0.09 mmol) in 1/1 dichloromethane/methanol (0.3 mL), followed by acetic acid (20 muL, 0.35 mmol) and the mixture was stirred at 50 C. for 15 minutes. MP-cyanoborohydride resin (327 mg, 0.07 mmol) was added and the mixture was shaken at 50 C. overnight, filtered and concentrated. To the residue was added 4M hydrogen chloride in dioxane (2 mL) and the mixture was shaken at 50 C. for 2 hours. The mixture was concentrated, dissolved in 1:1 dimethylsulfoxide/methanol and purified by preparative HPLC (Phenomenex Luna C8(2) 5 mum 100 AXIA column) eluting with a gradient of 5-100% acetonitrile/0.1% trifluoroacetic acid in water to afford the title compound as the trifluoroacetate salt. 1H NMR (400 MHz, pyridine-d5) delta 12.04 (s, 1H) 8.74 (s, 1H) 8.69 (s, 1H) 8.49-8.51 (m, 1H) 8.46 (s, 1H) 7.18 (d, J=7.32 Hz, 1H) 6.91-6.96 (m, 2H) 4.53 (s, 2H) 3.91-4.03 (m, J=8.55 Hz, 1H) 3.63-3.71 (m, J=8.70, 8.70 Hz, 2H) 3.61 (s, 1H) 3.53-3.60 (m, 1H) 3.47 (t, J=8.39 Hz, 2H) 3.07-3.16 (m, 1H) 2.92 (t, J=8.54 Hz, 2H) 2.44 (s, 3H) 2.19-2.27 (m, J=2.44 Hz, 1H) 1.87-2.11 (m, J=28.08 Hz, 2H) 1.76-1.86 (m, J=14.34 Hz, 1H). MS (ESI) m/z 463 (M+H)+.

The synthetic route of 50866-30-3 has been constantly updated, and we look forward to future research findings.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6N2O

To a solution of N,N- bis(4-methoxybenzyl)ethanesulfonamide (Example 100.0, 73.13 g, 0.21 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) slowly via additional funnel, and the resulting mixture was stirred for 10 min. Next, a solution of 5-methylpyrazine-2-carbaldehyde (Example 106.1, 21.3 g, 0.17 mol, 1.0 equiv.) in anhydrous THF (150 mL) was added, and the mixture was stirred at the same temperature for 45 min and then stirred and allowed to warm to RT for 2 h. The reaction mixture was quenched by addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL) (Note: no product was observed in the ammonium chloride or brine layer). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford the initial product as an oil. The oil thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g as a white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) delta 8.61 (d, J = 1.5 Hz, 1H), 8.51 (d, J = 1.5 Hz, 1H), 7.22- 7.11 (m, 4H), 6.90- 6.80 (m, 4H), 6.10 (d, J = 5.9 Hz, 1H), 5.29 (dd, J = 5.9, 2.2 Hz, 1H), 4.36- 4.16 (m, 4H), 3.73 (app s, 6H), 3.70-3.66 (m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d, J = 7.0 Hz, 3H). LCMS (ESI positive ion) m/z: 472.4 (M+H)+; Further elution of the mixture with a gradient of 30 % to 35 % EtOAc in petroleum ether yielded Example 106.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDCl3) delta 8.62 (d, J = 1.6 Hz, 1H), 8.44 (d, J = 1.5 Hz, 1H), 7.25- 7.12 (m, 4H), 6.93- 6.82 (m, 4H), 5.17 (d, J = 7.1 Hz, 1H), 4.47 (d, J = 15.2 Hz, 3H), 4.14 (d, J = 15.4 Hz, 2H), 3.82 (s, 3H), 3.82 (s, 3H), 3.66- 3.61 (m, 1H), 2.60 (d, J = 2.0 Hz, 3H), and 1.08 (dd, J = 7.2, 2.1 Hz, 3H). LCMS (ESI pos.) m/z: 472.4 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 1a-9a (1.0mmol) was dissolved in toluene (70mL) in a flask which was wrapped with tin foil, sodium hydride (1.5mmol) and triethyl phosphonoacetate (1.0mmol) was added respectively. Then the reaction solution was stirred at room temperature under dark until TLC analysis showed complete conversion. Extracted with EtOAc, the combined organic phase was washed with saturated brine (50mL¡Á3), and dried over anhydrous sodium sulfate. Concentrated and purified by column chromatography (PE/EA=8: 1) to give a pale yellow solid (1b-9b). The synthetic routes are similar to PL [7,12].

The chemical industry reduces the impact on the environment during synthesis 5-Methylpyrazine-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zou, Yu; Yan, Chang; Zhang, Huibin; Xu, Jinyi; Zhang, Dayong; Huang, Zhangjian; Zhang, Yihua; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 313 – 319;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, These common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of N,Nbis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 mm. Then a solution of 5-methylpyrazine-2-carbaldehyde (Example 33.1, 21.3 g, 0.174 mol, 1.0 equiv.) in anhydrous THF (150 mL) was added, and the resulting mixture was stirred at the same temperature for 45 mm and then allowed to warm to RT for 2 h. The reaction mixture was quenched by the addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL) (Note: no productwas observed in the ammonium chloride or brine layer). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford an oil. The oil was purified by flash column chromatography (silica gel, 23 0-400 mesh) to afford the two isomers. The faster moving isomer (32 g as a white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) 0 8.61 (d, J 1.5 Hz, 1H), 8.51 (d, J= 1.5 Hz, 1H), 7.22-7.11 (m, 4H), 6.90-6.80 (m, 4H), 6.10 (d, J= 5.9 Hz, 1H), 5.29 (dd,J= 5.9, 2.2 Hz, 1H), 4.36-4.16 (m, 4H), 3.73 (m, 6H), 3.70-3.66(m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d,J= 7.0 Hz, 3H). LCMS-ESI (pos.) m/z:472.4 (M+H)t; Further elution of themixture with a gradient of 30 % to 35 % EtOAc in petroleum ether yielded Example 33.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDC13) oe 8.62 (d, J= 1.6 Hz, 1H), 8.44 (d,J= 1.5 Hz, 1H), 7.25-7.12 (m, 4H), 6.93-6.82 (m, 4H), 5.17 (d,J= 7.1 Hz, 1H), 4.47 (d, J= 15.2 Hz, 3H), 4.14 (d, J 15.4 Hz, 2H), 3.82 (d, J 1.8 Hz, 6H), 3.66-3.61 (m, 1H), 2.60 (d, J = 2.0 Hz, 3H), and 1.08 (dd, J = 7.2, 2.1 Hz, 3H). LCMSESI (pos.) m/z:472.4 (M+H)t

Statistics shows that 5-Methylpyrazine-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 50866-30-3.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, molecular formula is C6H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C6H6N2O

To a solution of N,N- bis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 min. A solution of 5-methylpyrazine-2-carbaldehyde (Example 33.1, 21.3 g, 0.174 mol, 1.0 equiv.) in anhydrous THF (150 mL) was then added, and the resulting mixture was stirred at the same temperature for 45 min and allowed to warm to RT for 2 h. The reaction mixture was quenched by addition of an aqueous ammonium chloride solution (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford an oil. The oil thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g as white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) delta 8.61 (d, J = 1.5 Hz, 1H), 8.51 (d, J = 1.5 Hz, 1H), 7.22- 7.11 (m, 4H), 6.90- 6.80 (m, 4H), 6.10 (d, J = 5.9 Hz, 1H), 5.29 (dd, J = 5.9, 2.2 Hz, 1H), 4.36- 4.16 (m, 4H), 3.73 (m, 6H), 3.70-3.66 (m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d, J = 7.0 Hz, 3H). LCMS-ESI (pos.) m/z: 472.4 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50866-30-3, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem