Month: June 2021

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. 6270-63-9, name is Pyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., Formula: C4H4N2O

General procedure: The appropriate nucleophile (1 equiv.), the epoxide (1-3 equiv.) and a base (1-5 equiv.) were suspended in a solvent and the reaction mixture was heated under the stated conditions. (0735) The reaction was allowed to cool to rt, saturated NH4CI(aq) or water was added and the resulting mixture was extracted using DCM or EtOAc (x 3). The combined organic extracts were dried (phase separator or MgS04), concentrated under reduced pressure and the remaining residue was purified by flash chromatography to give the product.

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; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 274-79-3, name is Imidazo[1,2-a]pyrazine, 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 274-79-3, Recommanded Product: Imidazo[1,2-a]pyrazine

General procedure: Imidazo[1,2-a]pyrazines (0.3 mmol), 2-chlorobenzaldehyde (0.33 mmol, 1.1 equiv.), K2CO3 (0.9 mmol, 3 equiv.), PivOH (30 mol%), Pd(OAc)2 (7.5 mol %), and Xantphos (15 mol %) were added to a 10 mL round-bottomed flask, and then a mixed solvent of 3 mL of DMF and 30 uL of H2O was added. The mixture was stirred under air at 110 C for 24 h. After the reaction was complete, the mixture was washed with water and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using dichloromethane/methanol as the eluent to give the pure product.

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, Imidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mu, Bing; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Chang, Junbiao; Wu, Yangjie; Tetrahedron Letters; vol. 58; 52; (2017); p. 4816 – 4821;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 72788-94-4, 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. 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Et3N (4.17 mL, 29.9 mmol) and mesyl chloride (1.57 mL, 20.3 mmol) were added to a solution of (5-chloro-2-pyrazinyl)methanol (45) (obtained by chlorination and reduction of 5-hydroxypyrazine-2-carboxylic acid, as reported by Kiener et al., 1994) (1.443 g, 9.98 mmol) in anhydrous THF (20 mL) at 0 0C. The mixture was stirred at 0 0C for 0.5 h, then partitioned between EtOAc and water. The organic fraction was dried (MgSO4) and the solvent was removed under reduced pressure to give the crude mesylate. The mesylate was dissolved in acetone (40 mL), sodium iodide (7.5 g, 50 mmol) was added, and the mixture was refluxed for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic fraction was concentrated under reduced pressure and the residue was chromatographed on silica gel (eluting with CH2Cl2) to give 2-chloro-5- (iodomethyl)pyrazine (46) (1.54 g, 61%), which was used immediately due to its instability.

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

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); 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. 109-08-0, name is 2-Methylpyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 109-08-0

To a solution of methyl picolinate (1.14 g, 1 mL, 8.3 mmol) and 2-methylpyrazine (0.78 g, 0.76 mL, 8.3 mmol) in THF (15 mL) was added NaH (60% in mineral oil, 0.5 g, 12 mmol). The mixture was refluxed for 16 h. Once cooled to room temperature, the mixture was poured into saturated aqueous solution of NH4CI (30 mL) and extracted with EtOAc (3 x 30 mL). Organic fractions were combined, washed with brine (30 mL), dried over MgS04, and the solvent was evaporated in vacuo. The product, purified by column flash chromatography (CTHC^MeOH; 10: 1 to 5: 1), was obtained as a yellow solid (1.3 g, 80 %). (‘ 11 NMR shows a mixture of the keto- and enol- forms in ratio ca. 1 : 1) (0265) NMR (500 MHz, CDC13) (ppm) 13.65 (s, 1H), 8.71 (ddd, / = 0.9, 1.8, 4.8 Hz, 1H), 8.67 – 8.64 (m, 2H), 8.58 (d, J = 1.1 Hz, 1H), 8.52 (dd, J = 1.6, 2.6 Hz, 1H), 8.46 (d, J = 2.6 Hz, 1H), 8.36 – 8.31 (m, 2H), 8.12 – 8.05 (m, 1H), 8.00 – 7.94 (m, 1H), 7.88 – 7.83 (m, 1H), 7.83 – 7.77 (m, 1H), 7.50 (ddd, J = (0266) 1.2, 4.7, 7.5 Hz, 1H), 7.32 (ddd, / = 1.2, 4.7, 7.5 Hz, 1H), 6.94 (s, 1H), 4.80 (s, 2H); (0267) 13C NMR (126 MHz, CDC13) d (ppm) 197.7, 162.0, 154.2, 152.9, 152.6, 152.1, 149.3, 149.3, 146.3, (0268) 145.2, 144.4, 142.9, 140.2, 140.0, 137.2, 137.2, 127.7, 124.4, 122.5, 120.5, 94.2, 44.5; (0269) HRMS calcd for C11H10N3O [M+H]+ 200.0818, found 200.0816.

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; MASARYKOVA UNIVERZITA; PARUCH, Kamil; CARBAIN, Benoit; HAVEL, Stepan; DAMBORSKY, Jiri; BREZOVSKY, Jan; DANIEL, Lukas; SISAKOVA, Alexandra; NIKULENKOV, Fedor; KREJCI, Lumir; (190 pag.)WO2019/201865; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 344940-70-1, name is 5-Bromo-3-phenylpyrazin-2-amine, 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 344940-70-1, Formula: C10H8BrN3

Step B: 5-Amino-6-phenylpyrazine-2-carbonitrileTo a deoxygenated solution of 5-bromo-3-phenylpyrazin-2-amine (1.00 g, 3.20 mmol) in NMP (15 mL) was added dicyanozinc (1.13 g, 9.61 mmol) and Pd(dppf)Cl2 (0.262 g, 0.320 mmol). The resulting mixture was heated at 150 C for 3 h then cooled and partitioned between water (10 mL) and EtOAc (15 mL x 3). The combined organic layers were dried over Na2S04 and concentrated, and the residue was purified by silica gel column chromatography (PE/EtOAc = 10/1, 5/1, 2/1) to give the title compound. MS: m/z = 196.9 (M + 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, 5-Bromo-3-phenylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4,Some common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

Example 9: (/?)-l-[(5-Methyl-pyrazin-2-yIcarbamoyl)-methyl]-3-(l-thiophen-2-yl5 cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane bromide To a mixture of 5-methyl-pyrazin-2-ylamine and cesium carbonate (11.2 g) dissolved dry DMF (30 mL) was added by dropwise addition bromoacetylbromide (2.89 g) and mixture stirred at rt for 2 hours. Water (200 mL) was added and the mixture extracted ethyl acetate (2 x 100 mL) and dried over magnesium sulfate. Concentration of the exi to -50 mL and addition of ts°hexane (100 mL) gave the sub-titled compound as a sol (1-64 g).1H NMR (400 MHz, DMSO-D6) delta 1 1.06 (IH, s), 9.17 (IH, s), 8.31 (IH, d), 4.16 (2H, 2.46 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylpyrazin-2-amine, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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 16298-03-6 as follows.

To a solution of methyl 3-amino- pyrazine-2- carboxylate (5.00 g, 32.7 mmol) in 1,2-dimethoxyethane (80 mL) were added ?2 (4.14 g, 16.3 mmol), copper(I) iodide (1.87 g, 9.80 mmol) and cesium iodide (8.48 g, 32.7 mmol) undernitrogen. Then isoamyl nitrite (13.2 mL, 98.0 mmol) was added dropwise at 20 °C. The reaction was stirred at 75 °C for 2 h, then quenched with water (100 mL). The aqueous layer was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by silica gel chromagraphy eluting withPE/EtOAc (5i02, PE: EtOAc = 1: O1O:1, v/v) to give the title compound. MS (ESI) mlz:264.7 [M+Hj ?H NMR (400MHz, DMSO-d6) oe = 8.71 (d, J=2.2 Hz, 1H), 8.63 (d, J2.0Hz, 1H), 3.93 (s, 3H)

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MILLER, Michael; CHOBANIAN, Harry, R.; HE, Shuwen; HAO, Jinsong; PIO, Barbara; GUO, Yan; XIAO, Dong; (213 pag.)WO2018/118670; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-amino-6-chloropyrazine (5 g, 38.60 mmol) in a mixture of anhydrous chloroform (120 mL), anhydrous acetonitrile (12 mL) and anhydrous methanol (12 mL) was addedslowly, at 0CC, NBS (7.56 g, 42.45 mmol, 1.1 eq.) and the mixture was warmed to room temper-ature and continuously stirred for 1 h. The excess solvent was removed in vacuo and the obtained crude material (light brown solid) was purified by column chromatography (Hexane/DCM/MeOH = 50/50/0 then 0/1 00/0 then 0/95/5) to afford 5-bromo-6-chloropyrazin-2-amine(6.34 g, 30.42 mmol, 79percent) as white crystals. ESI-MS: 209.90 [M+H]+. 1 H NMR (300 MHz,CDCI3) 6 7.69 (s, 1 H), 4.78 (br s, 2H).

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

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (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. 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Chloro-2,5-dimethylpyrazine

Intermediate 18: 3,6-d imethyllyrazin-2-amineAmmonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165 C for 7 hours. Following LCMS analysis, the reaction was then reheated to 165 C for a further 16 hours, by microwaves. After cooling, thesolvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20mL). Water (25 mL) was added and the mixture basified to pHl4 using sodium hydroxide solution(18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5 x25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated invacuoto give the title product (109 mg). This was used directly in the next step with no furtherpurification. LCMS (2 mm, high pH) Rt 0.47 mi m/z (ESj 124 (M+H).1H NMR (400 MHz, CHLOROFORM-o) O ppm 7.73 (5, 1 H), 4.42 (br. s., 2 H), 2.37 (5, 3 H), 2.35 (5, 3H).

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 95-89-6.

Reference:
Patent; GLAXO GROUP LIMITED; BIRAULT, Veronique; CAMPBELL, Amanda, Jennifer; HARRISON, Stephen; LE, Joelle; SHUKLA, Lena; WO2013/160419; (2013); 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 24241-18-7

The compound 3,5-dibromo-2-aminopyrazine 1a (20.0 g, 106 mmol) was added to aqueous ammonia (100 mL), and the reaction mixture was reacted at 110 C overnight, and the reaction was monitored by LCMS.Pour the reaction system into water (300 mL), extracted with ethyl acetate (500mLx2), the combined organic phases were saturated brine (200mL), dried over anhydrous sodium sulfate and concentrated.The crude product by column (v / v, petroleum ether / ethyl acetate = 30: 1-2: 1) to give the title compound 1b (9.0g, 47.8mmol), 60% yield

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem