Category: Pyrazines

Synthetic Route of 5049-61-6, A common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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 avoid over chlorination, milder conditions were examined. No reaction was observed at RT, but a complete transformation into the dichloro derivative was observed at 50C.

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; THE GOVERNMENT OF THE UNITED STATES, as represented by the secretary of HEALTH AND HUMAN SERVICES; WO2007/124345; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 21948-70-9, These common heterocyclic compound, 21948-70-9, name is 2-Methylthiopyrazine, 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 solution of AgClO4 (137mg, 0.67mmol) in MeCN (1mL), 2-methylthiopyrazine (84mg, 0.67mmol) was added and the mixture was stirred at ambient temperature for 5min. The resulting solution was filtered and Et2O (6mL) was then layered on a filtrate. The mixture was left overnight at 5C. The precipitated X-ray quality crystals were collected and dried in air. Yield: 210mg (95%). FT-IR (KBr, cm-1): 413 (w), 432 (vw), 494 (vw), 625 (s), 696 (vw), 741 (w), 762 (w), 843 (m), 974 (m), 1084 (vs), 1144 (s), 1292 (w), 1393 (w), 1441 (w), 1466 (w), 1508 (w). Anal. Calcd: C10H12Ag2Cl2N4O8S2 (663.76): C, 18.0; H, 1.8; N, 8.4; S, 9.6 Found: C, 18.2; H, 1.9; N, 8.5; S, 9.8.

Statistics shows that 2-Methylthiopyrazine is playing an increasingly important role. we look forward to future research findings about 21948-70-9.

Reference:
Article; Rogovoy, Maxim I.; Berezin, Alexey S.; Kozlova, Yuliya N.; Samsonenko, Denis G.; Artem’ev, Alexander V.; Inorganic Chemistry Communications; vol. 108; (2019);,
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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H4N2O2

Concentrated sulfuric acid (1.20 mL) was added slowly with vigorous agitation to a mixture of 2.48 g (20 mmol) of 2-pyrazine carboxylic acid (1) and 32 mL (1 mol) of methanol. The mixture was then reux for 12 h. Excess methanol was removed by evaporation and the residue was washed with water. The organic layer was again treated with water and concentrated sodium bicarbonate solution to an alkaline reaction, and then again with water. The product was dried over anhydrous MgSO4, collected by ltration, and distilled.

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 98-97-5.

Reference:
Article; Zhang, Fei; Wen, Qing; Wang, She-Feng; Shahla Karim, Baloch; Yang, Yu-Shun; Liu, Jia-Jia; Zhang, Wei-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 90 – 95;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit. Methyl 3,5-diamino-6-phenylpyrazine-2-carboxylate (3a) General Method A using 2 (500 mg, 2.47 mmol) and phenylboronic acid (360 mg, 3.70 mmol) to give 3a (412 mg, 68%) as an off-yellow solid. MP 194-196 C; 1H NMR (500 MHz, DMSO-d6) delta 7.54 (s, 2H), 7.44 (s, 2H), 7.37 (s, 1H), 7.08 (s, 2H), 6.66 (s, 2H), 3.74 (s, 3H); 13C NMR (126 MHz, DMSO-d6) delta 167.3, 156.0, 154.5, 137.6, 130.1, 128.9, 128.5, 128.1, 111.7, 51.4; IR (neat) nu 3435.3, 3319.6, 3160.5, 2948-2852, 1684.9, 1650.1, 1595.2, 1246.1, 708.2, 646.1 cm-1; HRESI-MS m/z (M + H+) Anal for C12H13N4O2+ 245.1033, found 245.1051.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 56423-63-3, 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 56423-63-3 as follows.

Under nitrogen atmosphere,4-nitrochlorobenzene (10 mg, 0.5 mmol),Potassium ethyl xanthate(80 mg, 0.5 mmol),N, N-dicarboximide (2 ml) was added to the dried reaction tube,The reaction was stirred for 2 h at 40 C in an oil bath.After the reaction system was cooled to room temperature,2-Bromopyrazine (80 mg, 0.5 mmol) was added to the reaction tube,Suspended in oil bath at 80 C for 12 h.After the reaction system was cooled,15 ml of 7K,The aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined,The solvent was evaporated under reduced pressure,Column chromatography gave a yellow solid(4-nitrophenyl)(2′ – pyrazinyl)Sulfide (lllmg, received95%).

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yichun University; Zhu, Qiming; Yuan, Qinghe; Chen, Ye; (9 pag.)CN105218418; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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. HPLC of Formula: C4H4ClN3

To a solution of 2-amino-6-chloropyrazine (6 g.) in acetonitrile (50 ml.) was added 2,2,2-trifluoroethylisothiocyanate (6 ml.) and the mixture heated under reflux on a steam bath for 6 hours. The mixture was allowed to cool, the resulting solid filtered and recrystallized from toluene to give 2-chloro-6-(3-[2,2,2-trifluoroethyl]thioureido)pyrazine.

The synthetic route of 2-Amino-6-chloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; US4447441; (1984); A;,
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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Pyrazinecarbonitrile

Pyrazine-2-carbonitrile 1g (10.5 g, 100 mmol) was dissolved in 150 mL of 1,4-dioxane under stirring, then Raney nickel (1.0 g) was added into a 250 mL autoclave. The reaction mixture was hydrogenated for 8 hours under 40 atmosphere at 60 C, filtered and concentrated under reduced pressure to obtain the title compound C-pyrazin-2-yl-methylamine 1h (10.7 g, yield 98%) as a brown oil. MS m/z (ESI): 110 [M+1]

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 19847-12-2.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2230241; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, 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. Safety of 5-Chloropyrazine-2-carboxylic acid

Step 2: Preparation of 5-methoxypyrazine-2-carboxylic acid [0171] To a solution 5-chloropyrazine-2-carboxylic acid (7 g, 44.15mmol) in methanol (55 mL) was added concentrated sulphuric acid (0.4 mL) and heated at 65 C for 4 h. The reaction mixture was cooled to room temperature and diluted with methanol (15 mL). Then a solution of sodium methoxide in methanol (8.58 g , 158.94 mmol, 35 mL) was added and the reaction mixture was stirred at room temperature for 30 minutes. Sodium hydroxide (2.825 g , 70.643mmol) in 30 ml water was added into the reaction mixture followed by addition of 40 mL water. Then the reaction mixture was heated at 40 C for 1 h and concentrated to remove methanol. The residue was diluted with water, acidified with 38% aqueous hydrochloric acid solution (pH 2-3) and extracted ethyl acetate (600 mL x 3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound 5-methoxypyrazine-2-carboxylic acid (6.43 g, 94% yield) as an orange solid. Calculated M+H: 155.04; Found M+H: 155.1.

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

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; MENNITI, Frank S.; WO2015/48507; (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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H8ClF3N4

2,4, 5-TRIFLUOROPHENYLACETIC acid (2-1) (150 g, 0.789 MOL), Meldrum’s acid (125 g, 0.868 mol), and 4- (DIMETHYLAMINO) pyridine (DMAP) (7.7 g, 0063 mol) were charged into a 5 L three-neck flask. N, N-DIMETHYLACETAMIDE (DMAC) (525 mL) was added in one portion at room temperature to dissolve the solids. N, N-DIISOPROPYLETHYLAMINE (282 mL, 1.62 mol) was added in one portion at room temperature while maintaining the temperature below 40 C. Pivaloyl chloride (107 ML, 0.868 mol) was added dropwise over 1 to 2 h while maintaining the temperature between 0 and 5 C. The reaction mixture was aged at 5 C for 1 h. Triazole hydrochloride 1-4 (180 g, 0.789 mol) was added in one portion at 40-50 C. The reaction solution was aged at 70 C for several h. 5% Aqueous sodium hydrogencarbonate solution (625 ML) was then added dropwise at 20-45 C. The batch was seeded and aged at 20-30 C for 1-2 h. Then an additional 525 mL of 5% aqueous sodium hydrogencarbonate solution was added dropwise over 2-3 h. After aging several h at room temperature, the slurry was cooled to 0-5 C and aged 1 h before filtering the solid. The wet cake was displacement-washed with 20% aqueous DMAC (300 mL), followed by an additional two batches of 20% aqueous DMAC (400 mL), and finally water (400 mL). The cake was suction-dried at room temperature. The isolated yield of final product 2-3 was 89%.

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/3135; (2005); A1;,
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 939412-86-9 as follows. Product Details of 939412-86-9

(f) (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxooctahydroindolizine-6-carboxamide HATU (15.91 g, 41.8 mmol) was added to a stirred, cooled 0 C. mixture of (6R,8aS)-3-oxooctahydroindolizine-6-carboxylic acid (7.3 g, 39.8 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (7.89 g, 43.8 mmol) and DIPEA (10.44 ml, 59.8 mmol) in CH2Cl2 (25 ml) and the mixture was stirred at room temperature for 1 h. and then concentrated. The residue was purified by column chromatography on silica gel (Isco 240 g silica gel), eluting with CH2Cl2/MeOH (50/1) to give (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxooctahydroindolizine-6-carboxamide (11.15 g, 36.1 mmol, 91% yield) as a white solid. LC-MS: Ret. time 1.09 min; m/z 309.11 (M+H)+; 1HNMR (CDCl3, 500 Hz): 8.38 (1H, d, J=2 Hz), 8.25 (1H, d, J=2 Hz), 7.37 (1H, dd, J=4 and 4.5 Hz), 4.56-4.72 (2H, m, 1), 4.29 (1H, dd, J=13 and 4.5 Hz), 3.42-3.47 (m, 1), 2.81 (1H, t, J=13 Hz), 2.35 (2H, t, J=8 Hz), 2.17-2.23 (1H, m), 2.04 (1H, d, J=13.5 Hz), 1.94-1.96 (1H, m), 1.74-1.82 (1H, m), 1.55-1.62 (1H, m), 1.16-1.24 (1H, m).

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem