54013-07-9

GENERAL METHOD: 5-Chloropyrazin-2-amine (0.2 g, 1.54 mmol) was dissolved in methanol (3 mL), and copper powder (0.13 g, 2.07 mmol) and a methanolic solution of sodium methanolate (0.38 mL, 1.75 mmol) were added sequentially. The reaction mixture was placed in a sealed tube and the reaction was stirred at 150 °C for 24 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under vacuum to obtain the crude product. The crude product was purified by silica gel column chromatography (100-200 mesh, methanol: dichloromethane, 2-3%) to afford the target compound 2-amino-5-methoxypyrazine (0.13 g, 67% yield).LC-MS (ES+) analysis showed m/z 126 ([M+H]+) with a retention time of 1.06 min (Method 1).

[1] Patent: WO2013/68458, 2013, A1. Location in patent: Page/Page column 45
[2] Patent: US2014/315885, 2014, A1. Location in patent: Paragraph 0242