Phenyl chloroformate → HCID 58138316, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol (1.0 g, 7.74 mmol) in CH3CN (20 mL) was added BSA (2.84 mL, 11.61 mmol), and the mixture was heated to 65° C. for 1 h. The resulting solution was cooled to room temperature and to it was added phenyl chloroformate (2.4 mL, 19.35 mmol) causing a slight exotherm. The mixture was stirred at room temperature overnight. The suspension that formed was suction filtered, and the solid was washed with Et2O (3×10 mL). The solid was suspended in Et2O (10 mL) for 2 h, was collected via suction filtration and was air-dried overnight. Phenyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.90 g, 47%) was isolated as a white solid: mp 175-180° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.25 (br s, 2H), 8.45 (d, J=7.25 Hz, 1H), 7.49-7.43 (m, 2H), 7.35-7.28 (m, 3H); ESIMS m/z 250 ([M+H]+).

Provenance & Evidence