Application of 14508-49-7, These common heterocyclic compound, 14508-49-7, name is 2-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.
t-Butyl 4-hydroxypiperidine-1-carboxylate (3.73 g, 18.0 mmol) was added to a N,N-dimethylformamide suspension (10 ml) of 60% sodium hydride (533 mg, 14.0 mmol), at 0C, and stirring was carried out at room temperature for 30 minutes. Chloropyrazine (1.15 g, 10.0 mmol) was further added at room temperature, and stirring was carried out for 1.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate and subsequent sequential washing with water and saline, and the resulting organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to afford t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate (2.79 g, yield 100%) as a white solid. 1H-NMR (CDCl3, 400 MHz) delta: 8.20 (1H, s), 8.10 (1H, d, J=2.8 Hz), 8.05 (1H, dd, J=2.8 Hz, 1.2 Hz), 5.24-5.18 (1H, m), 3.82-3.76 (2H, m), 3.33-3.27 (2H, m), 2.02-1.97 (2H, m), 1.79-1.70 (2H, m), 1.48 (9H, s). MS (ESI, m/z): 224 (M-tBu+H)+.
The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem