Pyrazines

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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 3,5-Dibromo-1-methylpyrazin-2(1H)-one

A mixture of tert-butyl 6-amino-3,4-dihydroisoquinoline-2(lH)-carboxylate (3 g, 12mmol), 3,5-dibromo-l-methylpyrazin-2(lH)-one (2.68 g, lOmmol), and triethylamine (1.5 g, 15mmol) in IPA (50 mL) was heated at 70¡ãC for 15 h. The mixture was cooled to room temperature. The resulting yellow solids were collected by filtration and dried in vacuum to afford 120a as a yellow solid (2.83 g, 65 ).MS: [M+H]+ 435.

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 13924-95-3

Step 1: (0546) To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100 C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methy-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

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; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); A1;,
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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 54608-52-5 as follows. Application In Synthesis of 2-Hydrazinopyrazine

Example 2: Synthesis of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol- 1 -yl)-N’-(pyrazin-2-yl)acr lohydrazide (1-3 .A 50-mL, 3-necked, round-bottomed flask was charged with a suspension of (Z)-3-(3- (3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l-yl)acrylic acid (0.200 g) in 1 :1 CH2C12: AcOEt (25 mL). 2-Hydrazinopyrazine (0.062 g) was added at -40 C followed by T3P (50%) (0.432g) and DIPEA (0.147 g). The reaction mixture was stirred for 30 min at -40 C before being concentrated under reduced pressure (35 C, 20 mmHg). The crude oil was purified by preparative TLC using 5% MeOH in CH2C12 as mobile phase (under ammonia atmosphere) to afford 40 mg (yield: 16%) of (Z)-3-(3-(355-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l- yl)-N’-(pyrazin-2-yl)acrylohydrazide. 1H NMR (400 MHz, DMSO-d6) delta ,10.53 (s, 1H), 9.59 (s, 1H), 9.14 (s, 1H), 8.53 (s, 2H), 8.29 (s, 1H), 8.13 (s, 1H), 8.06-8.07 (m, 1H), 7.92-7.93 (d, J=2.8 Hz, 1H), 7.51-7.53 (d, J=10.4 Hz, 1H), 6.07-6.10 (d, J=10.4 Etazeta,IotaEta); LCMS for CnHi2F6N70 [M+H]+ predicted: 444.31, found: 444.49 (RT 2.70 min, purity: 95.78%).

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; MCCAULEY, Dilara; SHECHTER, Sharon; WO2013/19548; (2013); A1;,
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Related Products of 4744-50-7, 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 4744-50-7 as follows.

17a. 3-(N-(2-Methyl-2-sulfanylpropyl)carbamoyl)pyrazine-2-carboxylic acid A suspension of 2-mercapto-2-methyl-1-propylamine hydrochloride (1.14 g, 8 mmol) in dichloromethane (15 mL) was cooled to 0 C. and then treated with triethylamine (1.23 mL, 0.9 g, 8.9 mmol) followed by furano(3,4-b)pyrazine-5,7-dione (1.2 g, 8 mmol). The reaction mixture was stirred at 0 C. for 40 minutes then at room temperature for 1 hour. The solvent was removed by evaporation and the residue triturated with hexane/ether to give the title compound (1.2 g, 59%). Mp 141-144 C. 1H NMR (300 MHz, DMSO-d6) delta8.83-8.86 (m, 3H), 3.45 (d, J=6.4 Hz, 2H), 2.87 (s, 1H), 1.33 (s, 6H).

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fang, Xinqin; Garvey, David S.; Gaston, Ricky D.; Lin, Chia-En; Ranatunga, Ramani R.; Richardson, Stewart K.; Wang, Tiansheng; Wang, Weiheng; Wey, Shiow-Jyi; US2003/203915; (2003); A1;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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. Formula: C5H4N4

To a stirring mixture of 5-aminopyrazine-2-carbonitrile (433 mg, 3.61 mmol) in THF (10 mL) was slowly added sodium hydride (240 mg, 6.02 mmol) below 15 C. The reaction mixture was stirred at room temperature for 1 h. To the above mixture was added compound 305-3 (1.0 g, 3.01 mmol). The resulting mixture was stirred at 60 C for 4 h. The reaction mixture was quenched with ice-water and extracted with ethyl acetate. The organic layer was dried over Na2504 and concentrated to afford the title compound 306-3 (1.5 g, crude) as a yellow oil. LCMS:405.0[M+1].

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

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
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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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

A mixture of 3,5-dibromo-l-methyl-2(lH)pyrazinone (1) (21.3g;79.5mmol), ethyl 4-aminobenzoate (13. Ig; 79.5mmol), and l-methyl-2-pyrollidinone (1OmL) was heated at 130 degrees for lhr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown solid. This was slurried with 0.5N NaOH, filtered, washed with water and diethyl ether to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl ester (2) as a light brown solid (21.3g); A mixture of 3,5-dibromo-l-methyl-2(lH)pyrazinone (21.3g;79.5mmol), ethyl 4-aminobenzoate (13. Ig; 79.5mmol), and l-methyl-2-pyrrolidinone (1OmL) was heated at 130 degrees for lhr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown solid. This was slurried with 0.5N NaOH, filtered, washed with water and diethyl ether to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl ester (1) as a light brown solid (21.3g)

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WHITNEY, James A.; DI PAOLO, Julie; VALLECA, Mark A.; BRITELLI, David R.; CURRIE, Kevin S.; DARROW, James W.; KROPF, Jeffrey E.; LEE, Tony; GALLION, Steven L.; MITCHELL, Scott A.; PIPPEN, Douglas A.I.; BLOMGREN, Peter A.; STAFFORD, Douglas Gregory; WO2008/33858; (2008); A2;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87597-27-1, These common heterocyclic compound, 87597-27-1, name is Ethyl 5-bromoimidazo[1,2-a]pyrazine-2-carboxylate, 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.

The mixture of 5-bromo-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester (0.3 g, 0.0011 mol), 3-biphenyl boronic acid (0.329 g, 0.0017 mol), (2′,6′-dimethoxy-biphenyl-2-yl)- dicyclopentadienyl-phosphane (0.091 g, 0.00022 mol), palladium acetate (0.025g, 0.00011 mol) and potassium phosphate (0.71 g, 0.0033 mol) in terahydrofuran (7 mL) was stirred at ambient temperature under continuous nitrogen flow for 20 hours. A solution of lithium hydroxide monohydrate (0.2g, 0.0048 mol) in 5 mL of water was added and the stirring at ambient temperature was continued for another 4 hours. The solvents were removed and the residue was subjected to to preparative RP-HPLC (10% to 40% acetonitrile/0.05M aqueous ammonium acetate, buffered to pH 4.5, over 30 min at 21 mL/min; No. = 254 nm; Microsorb C18, 100 A, 5 mum, 250 x 46 mm column) to yield 5-biphenyl-4-ylmethyl-imidazo[1,2- a] pyrazine-2-carboxylic acid (0.049 g, 0.00016 mol) as an off-white solid. Retention time – 1.22 min., RP-HPLC (30% to 95% acetonitrile/0.01M aqueous ammonium acetate, buffered to pH 4.5, over 4.5 min at 0.8 mL/min; No. = 190-700 nm; Genesis C18,120 A, 4 mum, 33 x 4.6 mm column.). m/z: (M – H)-314.

The synthetic route of 87597-27-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4430-75-5, The chemical industry reduces the impact on the environment during synthesis 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

General procedure: 5.1.2. General procedure 1 (GP1). The amine (1.0equiv) in ethanol (1mL per mmol amine) was added to the alkyl halide (1.1equiv) and sodium carbonate (3equiv) in ethanol (2mL per mmol amine). The reaction was heated to reflux for 2-3h then water (5mL per mmol amine) and aqueous sodium carbonate (1M, 5mL per mmol amine) were added. The product was extracted with ethyl acetate (3 times, 20mL per mmol amine) and the organic layers combined. Dowex 50WX2 hydrogen form 100-200 mesh (4g per mmol amine) was washed with methanol (10mL per gram resin). The reaction mixture was loaded onto the ion exchange resin using gravity filtration and the resin was washed with methanol (10mL per gram resin). The product was eluted off the resin with ca. 1M NH3 in methanol (10mL per gram resin) and the solution was concentrate to give the 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, Octahydro-2H-pyrido[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kelly, Nicholas M.; Wellejus, Anja; Elbr¡ãnd-Bek, Heidi; Weidner, Morten Sloth; J¡ãrgensen, Signe Humle; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3334 – 3347;,
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Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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. 5-vinylpyrazin-2-amine; To a mixture of 5-bromopyrazin-2-amine (1.0 g, 5.78 mmol) and vinyltri-n-butyltin (2.01 g, 6.36 mmol) in DMF(19 mL) were added LiCl (269 mg, 6.36 mmol) and DIEA (1.1 mL, 6.36 mmol). After degassing for 20 minutes, Pd(PPh3)4 (400 mg, 0.35mmol) was added to the reaction mixture. And then the mixture was refluxed for 4 hours under Ar atmosphere. The reaction mixture was cooled to room temperature and stirred with a 10% aqueous solution of potassium fluoride for 1 hour. The resulting solution was filtered through a pad of celite and washed with ethyl acetated. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layer was dried over MgS04 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (30% to 50% Ethyl acetate/Hexane) to afford title product (540 mg, 77% yield). MS m/z : 122 [M+l].

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; WO2011/90738; (2011); A2;,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

Intermediate 22 5-Methoxypyrazin-2-amine [0242] To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150 C. in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH: DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 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, 2-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Brookings, Daniel Christopher; Ford, Daniel James; Franklin, Richard Jeremy; Ghawalkar, Anant Ramrao; Kulisa, Claire Louise; Neuss, Judi Charlotte; Reuberson, James Thomas; US2014/315885; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem