Imidazole → 4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine

Participants

Reaction Steps

2-[(2-Chloropyrimidin-4-yl)oxy]ethanol (416 mg, 2.38 mmol) in dichloromethane (9.5 mL) at 0° C. was added to an oven-dried, nitrogen cooled vial containing imidazole (389 mg, 5.72 mmol). The solution was stirred for 10 minutes. TBS-Cl (424 mg, 2.81 mmol) was added and the reaction mixture was stirred at room temperature for 2 h then, diluted with water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine as a clear, yellow oil. MS ESI calcd. for C12H22ClN2O2Si [M+H]+ 289. found 289. 1H NMR (500 MHz, CDCl3) δ 8.28 (d, J=5.7, 1H), 6.67 (d, J=5.7, 1H), 4.62-4.30 (m, 2H), 4.02-3.87 (m, 2H), 0.87 (s, 9H), 0.06 (s, 6H).

Provenance & Evidence