Benzyl chloroformate → HCID 58138308, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol* (0.5 g. 3.87 mmol) in acetonitrile (CH3CN; 10 mL) was added N,O-bis(trimethylsilyl)acetamide (BSA; 1.42 mL, 5.81 mmol), and the mixture was heated to 55° C. for 1.5 h. The resulting solution was cooled to room temperature and to it was added benzyl chloroformate (1.38 mL, 9.67 mmol) causing a slight exotherm. After 10 minutes (min), a white precipitate formed that was allowed to stir at room temperature overnight. The solid was suction filtered and was washed with diethyl ether (Et2O; 2×10 mL), CH3CN (1×3 mL) and again with Et2O (2×10 mL) to give benzyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.515 g, 50%) as a white solid: mp 212-215° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.35 (s, 1H), 8.07 (s, 1H), 8.04 (d, J=7.25 Hz, 1H), 7.48-7.45 (m, 2H), 7.41-7.34 (m, 3H), 5.32 (s, 2H); ESIMS m/z 264 ([M+H]+).

Provenance & Evidence