Category: 13301-04-7

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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 13301-04-7

To a solution of methyl 2,5-dibromo pyrazine carboxylate (40g, 135mmol) in toluene (300ml) were dropwise added K2CO3 (28g, 202mmol) and N-ethyl-N- cyclohexylamine (35g, 270mmol). The reaction mixture was refluxed at 120C for 3 with stirring, and then cooled to room temperature. After extraction with ethyl acetate, the organic layer thus formed was washed with 2N HCI and further with water. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to afford the title compound (46g, 99%). 1H NMR (400MHz, CDCI3) 8.15 (s, 1 H), 3.92 (s, 3H), 3.50 (, 3H), 1.81 (m, 4H), 1.66 (m, 2H), 1.57 (m, 2H), 1.28 (m 2H), 1.12 (t, 3H).

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; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 13301-04-7

To a solution of methyl 3,6-dibromopyrazine-2-carboxylate (8.4 g, 28.3 mmol) in MeCN (142 mL) was added (3Patent; REVOLUTION MEDICINES, INC.; LI, Jie Jack; KOLTUN, Elena S.; GILL, Adrian Liam; BUCKL, Andreas; WON, Walter; AAY, Naing; MELLEM, Kevin; TZITZILONIS, Christos; JOGALEKAR, Ashutosh; CREGG, James Joseph; (177 pag.)WO2019/75265; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13301-04-7,Some common heterocyclic compound, 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, molecular formula is C6H4Br2N2O2, 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.

General Procedures:Synthesis of compound (B) as described in the general reaction scheme; 3 ,6-dibromo-pyrazine-2- carboxylic acid.[00248] LiOH (655mg, 27mmol) is added to a solution of methyl-3-amino-2-pyrazine carboxylate (A) (J. Med. Chem. 1969, 12, 285-87) (2.7g, 9mmol) in THF:water:MeOH (18:4.5:4.5mL).The reaction is stirred at 50C for 30min, concentrated in vacuo, taken up in DCM and washed with IN HCl. The organic phase is dried over MgSO4 and concentrated in vacuo to afford compound (B). 1H NMR (250MHz, CDCl3) delta(ppm)8.70(lH, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,6-dibromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 13301-04-7

To a dimethylformamide (300 ml) solution of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (7.47 g, 25.2 mmol), potassium carbonate (3.48 g, 25.2 mmol) and 4-fluorothiophenol (2.42 ml, 22.7 mmol) were sequentially added at room temperature and the mixture was stirred at room temperature for 30 minutes. The reaction solution was charged with water, extracted with ethyl acetate and then washed (with water and brine in this order). The water phases were combined and re-extracted with chloroform. The organic phases were combined, dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 25:1 to 10:1] to obtain a mixture (9.29 g) of 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester, 3-bromo-6-1(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester and 3,6-bis[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester.

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; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3,6-dibromopyrazine-2-carboxylate

To a solution of methyl 2,5-dibromo pyrazine carboxylate (40g, 135mmol) in toluene (300ml) were dropwise added K2CO3 (28g, 202mmol) and N-ethyl-N- cyclohexylamine (35g, 270mmol). The reaction mixture was refluxed at 120C for 3 with stirring, and then cooled to room temperature. After extraction with ethyl acetate, the organic layer thus formed was washed with 2N HCI and further with water. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to afford the title compound (46g, 99%). 1H NMR (400MHz, CDCI3) 8.15 (s, 1 H), 3.92 (s, 3H), 3.50 (, 3H), 1.81 (m, 4H), 1.66 (m, 2H), 1.57 (m, 2H), 1.28 (m 2H), 1.12 (t, 3H).

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; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 13301-04-7

A mixture of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (5.00 g, 17 mm), THF (1 0 0 m 1), cooled to -7 8 C. A solution of Diisobutylaluminium hydride (34 ml, 34 mmol) was slowly added dropwise at -78 C for 2 h. The reaction was quenched at -78 C by addition of glacial acetic acid and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 3 N hydrochloric acid, the dichloromethane was added and the water was extracted and washed with saturated NaC1 The solution was washed, dried over anhydrous Na2S04, and the solvent was removed by distillation under reduced pressure. The residue was purified on a silica gel column to afford the title compound as an off-white solid

The synthetic route of 13301-04-7 has been constantly updated, and we look forward to future research findings.

Electric Literature of 13301-04-7, A common heterocyclic compound, 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, molecular formula is C6H4Br2N2O2, 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 dimethylformamide (15 ml) solution of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (see Patent Document: BE662507)(780 mg, 2.64 mmol), potassium carbonate (364 mg, 2.64 mmol)) and 4-fluorothiophenol (0.253 ml, 2.37 mmol) were sequentially added at room temperature and the mixture was stirred at room temperature for one hour. The reaction solution was charged with water, extracted with chloroform and then dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: chloroform hexane = 1:2 to 10:0] and purified by recycle preparative HPLC (LC-908 type, Japan Analytical Industry Co. , Ltd.) [developing eluent: chloroform] to obtain a mixture of 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester and 3-bromo-6-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (940 mg) in the form of a light yellow solid substance.

The synthetic route of 13301-04-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 13301-04-7, 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a dimethylformamide (160 ml) solution of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (4.0 g, 13.5 mmol), 4-fluorothiophenol(1.36 ml, 12.8 mmol)) and potassium carbonate (1.86 g, 13.5 mmol) were added and the mixture was stirred for 2 hours at room temperature. The reaction solution was poured into water, extracted with ethyl acetate and washed (with water and brine, in this order), dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 20:1 to 10:1] to obtain 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (1.62 g) in the form of colorless powder. MS (ESI/APCI Dual): 343 (M+1) 1H NMR (300 MHz, CDC13) delta ppm 4.06 (s, 3 H) 6.99 – 7.25 (m, 2 H) 7.41 – 7.59 (m, 2 H) 8.43 (s, 1 H)

The chemical industry reduces the impact on the environment during synthesis Methyl 3,6-dibromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3,6-dibromopyrazine-2-carboxylate

Step 1. Synthesis of Compound (B) as Described in the General Reaction Scheme; 3,6-dibromo-pyrazine-2-carboxylic Acid LiOH (655 mg, 27 mmol) is added to a solution of 3,6-dibromo-pyrazine-2-carboxylic acid methyl ester (A) (J. Med. Chem. 1969, 12, 285-87) (2.7 g, 9 mmol) in THF:water:MeOH (18:4.5:4.5 mL). The reaction is stirred at 5 C. for 30 min, concentrated in vacuo, taken up in DCM and washed with 1N HCl. The organic phase is dried over anhydrous MgSO4 and concentrated in vacuo to afford compound (B). 1H NMR (250 MHz, CDCl3) delta (ppm) 8.70 (s, 1H).

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; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 13301-04-7, 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 13301-04-7 as follows.

The compound 3,6-dibromopyrazine-2-carboxylic acid methyl ester 3b (12.0 g, 40.8 mmol) was dissolved in tetrahydrofuran (120 mL). The N2 was replaced 3 times, and the dry ice acetone was cooled to -70 C, DIBAL-H solution (81.6 mL, 122.4 mmol) was added dropwise, and the reaction was carried out at -70 C for 1 hour.The system was quenched by the addition of 1M hydrochloric acid, ethyl acetate was added and stirred for 20 min. Filtration, the filtrate was separated and the aqueous was extracted with ethyl acetate.The organic phase was combined, washed once with saturated brine and dried over anhydrous sodium sulfate, dried under reduced pressure to give the title compound 3c (8.0g, 30.3mmol) using a rotary evaporator, the yield was 74.3 %

According to the analysis of related databases, 13301-04-7, the application of this compound in the production field has become more and more popular.

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