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 41110-33-2 as follows. category: Pyrazines
A solution of lithium aluminium hydride (164.0 mL, 0.164 mol, 1.0 M in THF, 0.5 equiv.) was added to a suspension of methyl 5-methylpyrazine-2-carboxylate (50 g, 0.328 mol, 1.0 equiv.) in anhydrous THF (750 mL) at -78 C. (The internal temperature was kept below -72 C during the addition of lithium aluminium hydride). Upon completion of addition, the reaction mixture was left, to stir at -78 C for a further 20 min and was then quenched with glacial AcOH (50.0 mL) at the same temperature. The resulting mixture was warmed to RT and the volatiles were removed by evaporation under pressure. The residue was dissolved in 1.5 N HCl (500 mL) and extracted with DCM (2 x 2 L). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (2 x 500 mL), (Note: no product observed in HCl or aqueous sodium hydrogen carbonate solution) dried over anhydrous Na2SO4, and concentrated in vacuo, to yield the initial product as a brown oil. The residue was purified by column chromatography (silica gel 60-120 mesh) eluting with a gradient of 10% EtOAc in petroleum ether to provide the title compound as a pale yellow liquid (21.3 g, 53 %). TLC Info: (9.0/1.0 Petroleum ether/EtOAc). 1H NMR (400 MHz, CDCl3) delta 10.14 (s, 1H), 9.07 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.4 Hz, 1H), and 2.70 (s, 3H). LCMS (ESI positive ion) m/z: 123 (M+H)+.
According to the analysis of related databases, 41110-33-2, the application of this compound in the production field has become more and more popular.
Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Pyrazine – Wikipedia,
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