Pyrazines

Adding a certain compound to certain chemical reactions, such as: 6164-79-0, name is Methyl 2-pyrazinecarboxylate, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6164-79-0, Product Details of 6164-79-0

To a stirred solution of sodium methoxide (25% in MeOH, 27.54 mL, 72.4 mmol, 1 eq) in 90 mL of toluene at 110 C. in a 3-neck flask attached with a mechanical stirrer, condenser and dropping funnel was added a solution of methylpyrazine-2-carboxylate (10 g, 72.4 mmol, 1 eq) in 115 mL of methyl acetate, dropwise, over a period of ?35-40 min. A yellow precipitate was formed. Stirring was continued at 110 C. for 3 hrs. The reaction was cooled and the yellow precipitate was filtered and washed with a small quantity of toluene. This solid was taken into 200 mL of saturated ammonium chloride and 400 mL of EtOAc. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 6.52 g (50%) of methyl 3-oxo-3-(pyrazin-2-yl)propanoate as a yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Bhagirath, Niala; Kennedy-Smith, Joshua; Wilhelm, Robert Stephen; US2013/158049; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 193966-70-0, 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. 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0139j To a solution of methyl 5-(bromomethyl)pyrazine-2-carboxylate (0.5 g, 2.16 mmol) in tetrahydrofuran (20 mL) was added potassium trimethylsilanolate (0.11 g, 0.80 mmol) and the reaction mixture was stirred at 70 C for 45 minutes. The reaction mixture was diluted with water (30 mL), acidified with 1.5 M hydrochloric acid (pH 2-3) and extracted with ethyl acetate (50 mL x 3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude was purified by silica gel column chromatography using 3% methanol in dichloromethane as eluant, to afford the title compound 5-(bromomethyl)pyrazine-2-carboxylic acid (0.174 g, 37% yield) as a yellow solid. Calculated M+H: 218.02; Found M+H: 218.1.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 5-(bromomethyl)pyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyrazine – Wikipedia,
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Related Products of 6863-74-7, 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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-chloropyrazine-2-carbonitrile (lg, 7.17 mmol) in dioxane (15 mL) was added 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (2.21 g, 14.33 mmol), Na2C03 (1.52 g, 14.33 mmol), and Pd(dppf)Cl2 (40 mg, 0.072 mmol) under N2. The resulting mixture was stirred at 100 C overnight. After cooling to RT, the mixture was diluted with EtOAc (30 mL), washed with brine, dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (9% EtOAc in petroleum ether) to give the title compound as a solid. LRMS m/z (Mu+Eta) 132.1 found, 132.1 required.

The chemical industry reduces the impact on the environment during synthesis 6-Chloropyrazine-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (85 pag.)WO2016/100156; (2016); A1;,
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Pyrazine | C4H4N2 – PubChem

Reference of 4774-14-5,Some common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

j0662j To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture wasadded 2,6-dichloropyrazine (LXIII) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1-(6- chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXIV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17C1N402 mlz 285.1 (M+H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (300 pag.)WO2017/23972; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, 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. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(1R,2S)-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, Example 27.2 (1063) To a solution of N,N-bis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equivalent.) in anhydrous THF (600 mL) at -78 C. was slowly added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equivalent.) via additional funnel, and the resulting mixture was stirred for 10 min. Next, a solution of 5-methylpyrazine-2-carbaldehyde (Example 27.1, 21.3 g, 0.174 mol, 1.0 equivalent.) in anhydrous THF (150 mL) was added, and the mixture was stirred at the same temperature for 45 min and then allowed to warm to RT for 2 h. The reaction mixture was then quenched by addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2¡Á2 L). The combined organic layers were washed with brine (2¡Á500 mL). No product was observed in the ammonium chloride or brine layers. After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford the product as an oil. The product thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g) was obtained as a white solid 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)+. (1S,2S)-1-Hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide and (1R,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide, Example 28.3 (1064) Further elution of the mixture in Example 27.2 with a gradient of 30% to 35% 21 EtOAc in 201 petroleum ether yielded Example 27.3 (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 positive ion) m/z: 472.4 (M+H)+.

The synthetic route of 5-Methylpyrazine-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 486424-37-7, 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 486424-37-7 as follows.

CDI (2.23 g, 13.8 mmol) was added to a suspension of 3-amino-6-bromopyrazine-2- carboxylic acid (2.00 g, 9.17 mmol) in DMF (20 ml). The reaction was stirred at RT for 16h. The reaction mixture was cooled (0 00) then diluted with water (20 ml). The solid wascollected by filtration then washed with the minimum volume of water and cooled (0 00)MeCN then dried under vacuum to afford the product as a yellow solid (2.23 g, 86%).1H NMR (250 MHz, DMSO-d6) O 8.58- 8.52 (m, 2H), 7.96-7.82 (m, 3H), 7.15- 7.07(m, 1H). LC/MS (System A, MeOH quench): mlz (ESl) = 232 [Methyl ester M(79Br)H], 234 [Methyl ester M(81Br)H]), R = 0.87 mi UV purity = 95%.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; MCCARTHY, Clive; (108 pag.)WO2019/77340; (2019); 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. 426829-61-0, name is N-Benzyl-6-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H10ClN3

To a stirred solution of benzimidazole (130mg, 1. LMMOL) in anhydrous DMF (5mL) at 0C under N2 was added sodium hydride (56mg, 60% dispersion in oil, 1. 45MMOL) in portions over 2 min. The mixture was stirred at 0C for 15 min and at RT for 60 min. To this was added a solution of (6-CHLORO-PYRAZIN-2-YL)- (L-BENZYL)-AMINE (220mg) in DMF (5mL) and the resulting mixture was then heated at reflux for 18h. The DMF was removed under reduced pressure and the residue diluted with chloroform. The organic layer was washed with water, dried (Na2SO4) and the solvent removed under reduced pressure to furnish the crude product. Column chromatography using dichloromethane-methanol (20: 1 < 10: 1) as eluant separated the product (100mg). H-N. m. r. (CD3) 8 4.66 (d, 2H, J= 5.7Hz, CH2), 5.56 (m, 1H, NH), 7.29-7. 39 (m, 7H, Ar-H), 7.78-7. 89 (m, 2H, Ar-H), 7.92 (s, 1H, pyraz-H), 8.16 (s, 1H, pyraz-H), 8.48 (s, 1H, benzimid-H2). m/z (ES) 302 (M++H). Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 426829-61-0. Reference:
Patent; CYTOPIA PTY LTD; WO2003/99811; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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. Recommanded Product: 5-Methylpyrazine-2-carboxylic acid

General procedure: Under Argon, a stirred solution of carboxylic acid (0.37 mmol,1.0 eq.) and Et3N (0.48 mmol, 1.3 eq.) in dry THF (7 mL) was cooledto 10 C. Ethyl chloroformate (0.55 mmol, 1.5 eq.) was drop wiseadded and the resulting mixture was stirred for 2 h. Afterwards, asolution of sodium azide (0.63 mmol, 1.7 eq.) in water (2 mL) wasadded in one portion. After 1 h at 10 C, the reactionwas found tobe complete (TLC) and was quenched into iced water (5 mL). Themixture was extracted with EtOAc (3 10 mL) and the combinedorganic layers were successively dried over MgSO4, filtered andevaporated. The crude acyl azide was placed in dry toluene (20 mL)and heated at reflux for 1 h to give the corresponding crude isocyanate.The latter was placed in dry dioxane (7 mL) prior to addingthe appropriate amine 8, 9 or 10 (0.37 mmol, 1.0 eq.). The solutionwas heated at 100 C for 24 h. The reaction mixture was cooled andthe volatiles were removed to dryness in vacuum at 40 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5521-55-1, its application will become more common.

Reference:
Article; Boulahjar, Rajaa; Ouach, Aziz; Bourg, Stephane; Bonnet, Pascal; Lozach, Olivier; Meijer, Laurent; Guguen-Guillouzo, Christiane; Le Guevel, Remy; Lazar, Said; Akssira, Mohamed; Troin, Yves; Guillaumet, Gerald; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 274 – 287;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

l-Chloro-N,N,2-trimethyl-l-propenylamine (0.042 mL, 0.31 mmol) was added to a solution of 3- { [5-(azetidin- 1 -ylcarbonyl)pyrazin-2-yl]oxy }-5- { [(Ii?)- 1 -methyl-2- (methyloxy)ethyl]oxy}benzoic acid (0.102 g, 0.0.31 mmol) in DCM (3 mL) under argon and stirred at RT for 40 minutes. 2-Amino-5-methylpyrazine (57 mg, 0.52 mmol) and pyridine (0.043 mL, 0.52 mmol) were added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue taken up in ethyl acetate (30 mL), washed with water (2 x 10 mL), a saturated aqueous solution of sodium bicarbonate (10 mL), brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo. The crude material was chromatographed on silica, eluting with a gradient of 60-100% ethyl acetate in isohexane, to give the desired compound as a white foam (86 mg). SUP>1H NMR delta (CDCl3): 1.35 (d, 3H), 2.32 – 2.44 (m, 2H), 2.56 (s, 3H), 3.41 (s, 3H), 3.47 – 3.64 (m, 2H), 4.26 (t, 2H), 4.62 (q, IH), 4.69 (t, 2H), 6.98 (s, IH), 7.29 (s, IH), 7.41 (s, IH), 8.13 (s, IH), 8.35 (s, 2H), 8.86 (s, IH), 9.54 (s, IH); m/z 479 (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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H3BrN2

General procedure: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 56423-63-3.

Reference:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem