Category: Pyrazines

Electric Literature of 41110-34-3, 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. 41110-34-3, name is Ethyl 5-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Preparative Example 1 5.40 g of ethyl 5-methylpyrazine-2-carboxylate was dissolved in 54.0 mL of carbon tetrachloride, and 5.78 g of 1-bromosuccinimide and 267 mg of 2,2′-azobis(isobutyronitrile) were added thereto, followed by heating with reflux for 3 hours. The reaction liquid was left to be cooled to room temperature and then concentrated under reduced pressure, and the obtained residue was suspended in 100 mL of ethyl acetate and the insoluble materials were separated by filtration. The filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1) to obtain 2.62 g of ethyl 5-(bromomethyl)pyrazine-2-carboxylate.

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-methylpyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Astellas Pharma Inc.; EP2305641; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 14508-49-7, 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. 14508-49-7, name is 2-Chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-hydrazinopyrazine (820 mg, 7.45 mmol), prepared from 2-chloropyrazine and hydrazine using a procedure analogous to that described in the literature (P. J. Nelson and K. T. Potts, J. Org. Chem. 1962, 27, 3243, except that the crude product was extracted into 10% methanol/dichloromethane and filtered, and the filtrate was concentrated and purified by flash chromatography on silica gel, eluting with 100% ethyl acetate followed by 10% methanol in dichloromethane), TFA (2.55 g, 22.4 mmol), and polyphosphoric acid (10 mL) was heated to 140 C. with stirring for 18 h. The solution was added to ice and neutralized by the addition of ammonium hydroxide. The aqueous solution was extracted with ethyl acetate (3×), washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography (silica gel, 1:1 hexane:ethyl acetate, then 100% ethyl acetate) afforded the title compound as a solid (861 mg). 1H NMR (500 MHz, CDCl3) delta 8.17-8.20 (m, 2H), 9.54 (s, 1H). LC/MS (M+1) 189.

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

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 5521-55-1

A solution of compound A3-1 (30 g, 216 mmol), Boc20 (56.2 g, 260 mmol) and DMAP (7.9 g, 640 mmol) in t-BuOH (800 mL) was stirred at 60 C for 18 h. The solution was concentrated and purified by column (PE: EA = 3: 1) to afford compound A3-2 (40 g, 95%>). 1H NMR (400 MHz, CDC13): 9.05 (d, J= 1.2 Hz, 1H), 8.52 (d, J= 0.8 Hz, 1H), 2.60 (s, 3H), 1.60 (s, 9H).

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; GILBERT, Eric, J.; STAMFORD, Andrew, W.; WO2012/138734; (2012); 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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7F3N4

General procedure: Nucleophilic reagent (2 mmol), trimethylamine (5 mmol) and S3(2 mmol) were dissolved in N,N-dimethylformamide (2 mL) at 0 C.The reaction mixture was stirred for 2e10 h, poured into water(10 mL), and extracted by ethyl acetate (30 mL) in two times. Thecombined organic layer was washed by saturated brine andconcentrated to give the crude residue, which was purified byrecrystallization or flash chromatography.

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 486460-21-3.

Reference:
Article; Xing, Jing; Zhang, Rukang; Jiang, Xiangrui; Hu, Tianwen; Wang, Xinjun; Qiao, Gang; Wang, Junjian; Yang, Fengling; Luo, Xiaomin; Chen, Kaixian; Shen, Jingshan; Luo, Cheng; Jiang, Hualiang; Zheng, Mingyue; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 281 – 294;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5049-61-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5049-61-6 name is Pyrazin-2-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-amino pyrazine (20 g, 0.21 mmol) and DMSO (300 mL), was dissolved in water (10 mL), and the at ice bath N- iodosuccinimide ( 49.7 g, 0.22mmol) was added, after stirring for 30 minutes, stirred at room temperature for 12 hours. Ethyl acetate – extracted from the water, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) as eluant to afford the title compound (18.5 g, 40%) as a yellow solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Kowa Co., Ltd.; Watanabe, Toshiaki; Morimoto, Toshiharu; Ogiya, Tadaaki; Maejima, Takashi; (34 pag.)JP2015/54838; (2015); A;,
Pyrazine – Wikipedia,
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 4949-13-7 as follows. Recommanded Product: 2-Fluoropyrazine

A solution of 2-fluoropyrazine (0.247 mL, 3.06 mmol), 2-amino-1-(piperidin-1-yl)ethanone hydrochloride (710 mg, 3.98 mmol) and DIPEA (1.603 mL, 9.18 mmol) in acetonitrile (5 mL) was heated to 100 C for 16 h. The reaction mixture was concentrated and then dissolved in ethyl acetate (15 mL) and water (20 mL). The organic Layer was washed and separated. The aqueous layer was then washed with ethyl acetate (5 x 15 mL). The organic layers were combined, dried through a hydrophobic frit and concentrated in vacuo. The crude material was purified using silica chromatography with a gradient of 0-80 % (3:1 ethyl acetate:ethanol + 1 % triethylamine)/cyclohexane. The relevant fractions were combined and concentrated in vacuo to yield 1-(piperidin-1-yl)-2-(pyrazin-2-ylamino)ethanone (415 mg, 1.88 mmol, 61 % yield) as an orange solid. LCMS (High pH, ES+): tR = 0.67 min, [M+H]+ 221.16. 1H NMR (400 MHz, CDCl3) delta 1.55-1.64 (m, 4H), 1.65-1.73 (m, 2H), 3.39-3.44 (m, 2H), 3.60-3.66 (m, 2H), 4.13 (d, J = 3.79 Hz, 2H), 5.88 (br. s., 1H), 7.79 (d, J = 3.03 Hz, 1H), 7.95-7.98 (m, 1H), 8.02 (d, J = 1.26 Hz, 1H) 13C NMR (101 MHz, CDCl3) delta 24.4, 25.5, 26.2, 42.5, 43.3, 45.4, 132.6, 134.0, 141.4, 153.8, 166.6 HRMS: (C11H16N4O) [M+H]+ requires 221.1397, found [M+H]+ 221.1391 numax (neat): 3328, 2941, 2857, 1639, 1586, 1531, 1436, 1251, 1230, 1000, 820, 615 cm-1.

According to the analysis of related databases, 4949-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Law, Robert P.; Ukuser, Sabri; Tape, Daniel T.; Talbot, Eric P. A.; Synthesis; vol. 49; 16; (2017); p. 3775 – 3793;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

General procedure: A mixture of 2,3-dichloro compound (1, 1.256 mmol), 10% Pd/C (0.0125 mmol), CuI (0.0125 mmol), PPh3 (0.0502 mmol) and Et3N (1.8844 mmol) in EtOH (4 mL) was stirred for 15 min. To this was added an appropriate terminal alkyne (2, 1.256 mmol), under a nitrogen atmosphere and the mixture was stirred at 60 C for 2-4 h. After completion of the reaction, the mixture was diluted with EtOAc (3 x 10 mL). The organic layers were collected, combined, washed with cold water (2 x 15 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The crude product was then purified by column chromatography on silica gel using EtOAc / n-hexane as a solvent system.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kolli, Sunder Kumar; Nakhi, Ali; Medishetti, Raghavender; Yellanki, Swapna; Kulkarni, Pushkar; Ramesh Raju; Pal, Manojit; Bioorganic and Medicinal Chemistry Letters; vol. 24; 18; (2014); p. 4460 – 4465;,
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. 160252-31-3, name is 1-(5-Chloropyrazin-2-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClN2O

A mixture of (4-(3-(cyclopropylmethoxy)phenoxy)-2-fluorophenyl)methanol (200 mg), 1-(5-chloropyrazin-2-yl)ethanone (119 mg), sodium hydride (60% in oil, 41.6 mg) and THF (1 ml) was stirred at room temperature for 10 min, and heated under microwave irradiation at 100C for 1 hr. To the mixture was added water at 0C, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (65 mg). 1H NMR (300 MHz, CDCl3) delta 0.27-0.39 (2H, m), 0.60-0.69 (2H, m), 1.19-1.31 (1H, m), 2.66 (3H, s), 3.77 (2H, d, J = 6.9 Hz), 5.48 (2H, s), 6.57-6.65 (2H, m), 6.68-6.86 (3H, m), 7.19-7.29 (1H, m), 7.43 (1H, t, J = 8.4 Hz), 8.23 (1H, d, J = 1.2 Hz), 8.83 (1H, d, J = 1.3 Hz).

According to the analysis of related databases, 160252-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIZOJIRI, Ryo; ASANO, Moriteru; TOMITA, Daisuke; BANNO, Hiroshi; TAWADA, Michiko; NII, Noriyuki; GIPSON, Krista E.; MAEZAKI, Hironobu; TSUCHIYA, Shuntaro; IMAI, Mayumi; AMANO, Yuichiro; (100 pag.)EP3279183; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, molecular formula is C6H9N3, 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. Product Details of 297172-19-1

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.40 g, 0.98 mmol) and 5,6,7,8-tetrahydroimidazo[1 ,5-a]pyrazine (0.18 g, 1.48 mmol) in dioxane (16 ml_), Cs2C03 (0.96 g, 2.96 mmol) and RuPhos (0.09 g, 0.19 mmol) were added and the reaction mixture was purged with argon for 30 min. Pd2(dba)3 (0.09 g, 0.09 mmol) was added and the reaction mixture was heated in sealed tube at 1 10C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with H20 (100 ml.) and extracted with EtOAc (3 * 100 ml_). The organic layer was separated, washed with brine (100 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 0 to 5% MeOH in DCM) and by preparative HPLC to afford 2-(6,8-dihydro-5H-imidazo[1 ,5- a]pyrazin-7-yl)-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide (0.07 g, 14%) as a white solid. HPLC Purity: 98.3% MS (ESI) m/e [M+H]7Rt/%: 449.00/2.76/96.0% 1H NMR (400 MHz, DMSO-d6) delta 0.81 (t, J=6.60 Hz, 3H) 1.18 – 1.35 (m, 4H) 1.44 – 1.60 (m, 2H) 2.82 – 2.92 (m, 2H) 3.89 (t, J=5.38 Hz, 2H) 4.1 1 (d, J=4.40 Hz, 1 H) 4.19 (t, J=5.38 Hz, 2H) 4.71 (s, 2H) 6.83 (s, 1 H) 6.93 – 6.98 (m, 1 H) 7.04 (t, J=7.34 Hz, 1 H) 7.10 (d, J=1.47 Hz, 1 H) 7.31 (d, J=7.82 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.65 (s, 1 H) 7.87 (s, 1 H) 8.01 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 297172-19-1, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-3-morpholinopyrazin-2-amine

5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (300 mg, 1 eq) was suspended in EtOH (3 mL) and 2,3-dibromo-n-methylmaleimide (31 1 mg, 1 eq) was added. The reaction mixture was heated under microwave irradiation at 120 C for 4 h. On cooling, the mixture was filtered to give a yellow solid (50 mg,) which was heated at 150 C for 5 min under open air. On cooling, the mixture was purified by automated chromatography (Biotage, eluent: 2% to 10% MeOH in DCM) to obtain the expected product I-20 (22 mg) as a yellow solid.

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; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem