Pyrazines

Electric Literature of 36070-80-1, These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, 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.

A solution of compound 10 (216 mg, 1.36 mmol)in SOCl2 was heated to reflux overnight. The excess SOCl2 wasremoved by vacuum distillation. The residue was dissolved in CH2-Cl2 and carefully treated with a solution of 2-amino-6-methylpiridine(739 mg, 6.83 mmol) and NEt3 (275 mg, 2.7 mmol) in CH2Cl2.The mixture was stirred at rt overnight. After the reaction wascompleted, the mixture was extracted with CH2Cl2, washed withwater, brine, and dried over Na2SO4. The organic phase was concentratedin vacuo and the residue was recrystallized from 2-propanolto give compound 11a as a yellow solid (181 mg, 53%). 1HNMR (300 MHz, CDCl3) d: 9.96 (br s, 1H), 9.28 (s, 1H), 8.60 (s,1H), 8.19 (d, J = 9.0 Hz, 1H), 7.68 (t, J = 9.0 Hz, 1H), 6.99 (d,J = 9.0 Hz, 1H), 2.51 (s, 3H).

Statistics shows that 5-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 36070-80-1.

Reference:
Article; Zhao, Chao; Choi, You Hee; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kwang-Youl; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 789 – 801;,
Pyrazine – Wikipedia,
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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;,
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Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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. Quality Control of 5-Chloro-2,3-diphenylpyrazine

116] Step 1. 2-(1.1.2.2.3.3.4.4-dR-4-((5.6-Diphenylpyrazin-2-viyperdeutero-propan-2- yl)amino)butan-l-ol (12a). To a solution of commercially available 5-chloro-2,3- diphenylpyrazine (10) (0.56 g, 2.10 mmol) in NMP (2.1 mL) was added dis-aminoalcohol 11a (0.46 g, 3.15 mmol, 1.5 equiv, prepared as described in Example 8). The reaction vessel was sealed and heated to 190 0C for 15 hours, then cooled to ambient temperature. The mixture was diluted with ice water and extracted with Et2O (3 x 20 mL). The combined organic layers were washed successively with water and brine. The resulting organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 30-50% EtO Ac/heptane) to afford 12a (0.13 g, 16%). MS (M+H): 377.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41270-66-0, its application will become more common.

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott L.; MASSE, Craig E.; LIU, Julie F.; WO2011/17612; (2011); A1;,
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Pyrazine | C4H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 6966-01-4

0.15 eq. palladium (II) acetate and 0.2 eq. 1,1′-bis(diphenylphosphino)-ferrocene were combined in dimethylformamide under nitrogen and heated to 50 C. for 20 minutes. R3 and n are each as defined herein. The reaction was allowed to cool to room temperature and 1.0 eq. of the pyrazine, 1.5 eq. of the boronic acid and 1.15 eq. of triethylamine were added. The reaction was heated to 90 for 12 hours and allowed to cool to room temperature. The DMF was removed by rotary evaporation. The crude reaction mixture was dissolved in chloroform and washed twice with 1N aq. HCl and then twice with saturated aq. NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered and concentrated. Material was purified by silica gel chromatography using 100% chloroform as eluent.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2004/180905; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 5-chloropyrazine-2-carboxylate

Example 7[0142] [Formula 41] [0143]1) In tetrahydrofuran (75 mL) was dissolved methyl 5-chloropyrazin-2-carboxylate (2.589 g), 1M diisobutyl aluminum hydride-tetrahydrofuran solution (30 mL) was added dropwise to the solution at 0C, and the mixture was stirred at the same temperature for 15 minutes. To the mixture were added water and IN hydrochloric acid, then, a saturated aqueous sodium bicarbonate solution was added to the same to make the pH to 7. The mixture was filtered through Celite, and then, extracted with chloroform 3 times. The organic layer was separated, dried over anhydrous sodium sulfate, and the residue obtained by concentrating the same under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate=90: 10 to 65:35 to 50:50) to obtain (5-chloropyrazin-2-yl)methanol (465 mg). MS (m/z): 147/145 [M+H]+

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
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Synthetic Route of 87486-34-8, These common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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.

5-Bromo-3-(4-(1,4-dimethyl-3-oxopiperazin-2-yl)phenylamino)-1-methylpyrazin-2(1H)-one (14); A 100-mL three-neck round-bottomed flask equipped with a mechanical stirrer and reflux condenser was charged with (4) (780 mg, 3.56 mmol), 13 (998 mg, 3.73 mmol), cesium carbonate (2.36 g, 7.26 mmol) and 1,4-dioxane (40 mL). After bubbling nitrogen through the resulting solution for 30 minutes, Xantphos (0.162 g, 0.281 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.15 g, 0.165 mmol) were added, and the reaction mixture was heated at reflux for 16 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting residue was absorbed onto silica gel and purified by flash chromatography to afford a 57percent yield (818 mg) of 14 as an orange solid: mp 206-207¡ã C.; 1H NMR (500 MHz, CDCl3) delta 8.27 (bs, 1H), 7.72 (dd, 1H, J=2.0, 8.5 Hz), 7.36 (dd, 2H, J=2.0, 8.5 Hz), 6.73 (s, 1H), 3.71 (m, 1H), 3.69 (s, 1H), 3.52 (s, 3H), 3.21 (m, 1H), 3.01 (m, 1H), 2.97 (s, 3H), 2.67 (m, 1H), 2.19 (s, 3H); MS (ESI+) m/z 406 (M+H).

Statistics shows that 3,5-Dibromo-1-methylpyrazin-2(1H)-one is playing an increasingly important role. we look forward to future research findings about 87486-34-8.

Reference:
Patent; Zhao, Zhongdong; Zhichkin, Pavel E.; Stafford, Douglas G.; Kropf, Jeffrey E.; BLOMGREN, Peter A.; Currie, Kevin S.; Lee, Seung H.; Mitchell, Scott A.; Xu, Jianjun; Schmitt, Aaron C.; US2009/82330; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Formula: C5HCl2N3

To a cooled 0 C suspension of (3S,4S)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4- amine dihydrochloride (4.19 g, 17.2 mmol) in acetonitrile (86 mL) were added Hunig’s base (15.06 mL, 86.0 mmol) and 3,5-dichloropyrazine-2-carbonitrile (3 g, 17.2 mmol). The resulting mixture was stirred at 25C for 1 h. The volatiles were removed under reduced pressure to give a yellow oil which was used without further purification. MS (ES+) C14H18C1N50 requires: 307, found: 308 [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; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; JONES, Philip; CROSS, Jason; BURKE, Jason; MCAFOOS, Timothy; KANG, Zhijun; (154 pag.)WO2019/213318; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5ClN2

Compound C21 (500 mg, 2.22 mmol), 1-chloropyrrolo[1,2-a]pyrazine (339 mg, 2.22 mmol), cesium carbonate (796 mg, 2.44 mmol), and palladium(ll) acetate (53 mg,0.22 mmol) were combined in 1,4-dioxane (15 mL), and the solution was degassed with nitrogen for 15 minutes. Di-tert-butyl[3,4, 5,6-tetramethyl-2?, 4?,6?-tri(propan-2-yl) bi phenyl2-yl]phosphane (214 mg, 0.444 mmol) was added to the reaction mixture, which wasthen degassed for an additional 2 minutes. The reaction mixture was heated to 100 00 in a microwave reactor for 6 hours, whereupon it was cooled to room temperature andfiltered through diatomaceous earth. The filter cake was washed with ethyl acetate, andthe combined filtrates were concentrated in vacuo. Silica gel chromatography (Gradient:20% to 80% ethyl acetate in heptane) was followed by three triturations with heptane;the resulting material was purified again using silica gel chromatography (Gradient:50% to 70% ethyl acetate in heptane) to provide the product as a pale yellow solid.Yield: 361 mg, 1.06 mmol, 48%; 13. In this case, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene was used in lieu ofdi-teit-butyl[3,4, 5, 6-tetramethyl-2?, 4? ,6?-tri(propan-2-yl)biphenyl-2-yl]phosphane.14. 4-Bromo-3-fluorophenol was protected as its tri(propan-2-yl)]silyl ether, which was converted to [3-fluoro-4-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2- yl)phenoxy][tri(propan-2-yl)]silane using the chemistry described for synthesis of C2 from Cl. Suzuki reaction with 5-bromo-6-methylpyrim idine-4-carbonitrile, followed bydesilylation using tetraethylammonium fluoride, afforded the requisite 5-(2-fluoro-4- hydroxyphenyl)-6-methylpyrimidine-4-carbonitrile.

According to the analysis of related databases, 136927-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Chloro-3,5-dimethylpyrazine

Step 3: Synthesis of 3,5-Dimethyl-2-(4-naphthalen-2-yl-phenyl)pyrazine (abbreviation: Hdm2nppr)First, into a recovery flask equipped with a reflux pipe were placed 0.55 g of 2-chloro-3,5-dimethylpyrazine, 0.96 g of 4-(2-naphthyl)phenylboronic acid, 0.41 g of sodium carbonate, 0.018 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 50 minutes, so that heating was performed. Then, the reaction container was cooled to 50 C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and recrystallized using methanol, whereby Hdm2nppr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 85% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 3 is illustrated in the following (c-2).

The synthetic route of 38557-72-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2011/245495; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem