Category: 54013-07-9

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. 54013-07-9, name is 5-Methoxypyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7N3O

2-Chloro-3-nitro-5-(trifluoromethyl)pyridine (500 mg) was dissolved in 1,2-dimethoxyethane (7.4 ml), and thereto were added 5-methoxypyrazine-2-amine (414 mg), tris(dibenzylidene acetone)dipalladium (0) (101 mg), potassium phosphate (843 mg) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (87 mg), and the mixture was heated to 100 C. After the mixture was stirred all day and all night, it was kept standing to cool to room temperature, and water and chloroform were added thereto. After an insoluble material was filtrated, the organic layer was separated. After the organic layer was concentrated, the residue was purified by the silica gel column chromatography affording the compound 2 (502 mg).MS m/z 316[M+H]+, APCI(+)

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 54013-07-9.

Reference:
Patent; Mitsubishi Tanage Pharma Corporation; US2012/258951; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 54013-07-9,Some common heterocyclic compound, 54013-07-9, name is 5-Methoxypyrazin-2-amine, molecular formula is C5H7N3O, 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 0.5 – 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

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

Reference:
Article; Letourneau, Jeffrey J.; Stroke, Ilana L.; Hilbert, David W.; Cole, Andrew G.; Sturzenbecker, Laurie J.; Marinelli, Brett A.; Quintero, Jorge G.; Sabalski, Joan; Li, Yanfang; Ma, Linh; Pechik, Igor; Stein, Philip D.; Webb, Maria L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3601 – 3605;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 54013-07-9, 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 54013-07-9 as follows.

Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (26 mg, 0.084 mmol, prepared as described in Synthesis 62 and 63), 5-methoxypyrazin-2-amine (16 mg, 0.127 mmol), cesium carbonate (55 mg, 0.169 mmol), 4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene (3.9 mg, 7 mol%), and tris(dibenzylideneacetone)dipalladium chloroform complex (3.5 mg, 3.5 mol%) were added to a vial which was flushed with nitrogen and sealed. Anhydrous toluene (0.3 mL) and DMF (0.1 mL) were added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated by microwave irradiation at 1300C for 30 minutes. The cooled solution was diluted with methanol and adsorbed onto an lsolute SCX-II column. The column was washed with methanol, then with 2M ammonia in methanol. The basic fractions concentrated. Preparative TLC, eluting with ethyl acetate – methanol – concentrated ammonia 10:1:0.2, gave methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3- ylamino)nicotinate (5 mg, 15%) as an oil.1H NMR (500 MHz, MeOH) delta 8.56 (1 H, s), 8.43 (1 H, s), 7.93 (1 H, s), 7.00 (1 H, s), 3.95 (3H, s), 3.84 (3H, s), 3.62-3.70 (2H, m), 2.60 (3H, s), 2.20-2.38 (4H, m), 2.00-2.10 (3H, m), 1.73-1.84 (2H, m). LCMS (3) Rt 1.70 min; m/z (ESI+) 399 (MH+).

According to the analysis of related databases, 54013-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

54013-07-9, The chemical industry reduces the impact on the environment during synthesis 54013-07-9, name is 5-Methoxypyrazin-2-amine, I believe this compound will play a more active role in future production and life.

Example 1AX; Preparation of 2-ethyl-N-(5-methoxypyrazin-2-yl)-4-f4- (methylsulfonyl)phenoxyl-2H-indazole-6-carboxamide (1AX): To a solution of 5-methoxypyrazin-2-annine (167 mg, 1.34 mmol) in dry dichloroethane (2.0 ml_) was added dimethylaluminum chloride (2.67 ml_, 2.67 mmol) slowly at O0C under nitrogen. After addition, the mixture was stirred for 1 hour at room temperature and then added methyl 2-ethyl-4-(4- (methylsulfonyl)phenoxy)-2H-indazole-6-carboxylate (1-1 f-7,100.0 mg, 0.267 mmol). Then the mixture was heated to 60-700C overnight. The reaction mixture was cooled to room temperature, poured into potassium sodium tartrate (aq., 10 ml_), and extracted with ethyl acetate (10 ml_ 3 times). The combined organic layers were dried and concentrated under reduced pressure and purified by preparative HPLC to afford the title compound (1AX, 20.0 mg, yield: 16%) as a white solid.1H NMR (400 MHz, DMSO-d6): delta 1.46-1.49 (t, 3H), 3.15 (s, 3H), 3.88 (s, 3H), 4.43-4.49 (q, 2H), 7.20 (s, 1 H), 7.17-7.31 (d, 2H), 7.91 -7.93(d, 2H), 8.15(s, 1 H), 8.32(s, 1 H), 8.44 (s, 1 H), 8.88 (s, 1 H), 10.97 (s, 1 H). MS (M+1 ): 468.2.

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

Reference:
Patent; PFIZER INC.; CORBETT, Jeffrey Wayne; GUZMAN-PEREZ, Angel; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/103438; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem