Phenyl chloroformate → HCID 58138316, compound

Temperature

65 °C

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]+).

1. additionwas added BSA (2.84 mL, 11.61 mmol)
2. temperatureThe resulting solution was cooled to room temperature and to it
3. customThe suspension that formed
4. filtrationfiltered
5. washthe solid was washed with Et2O (3×10 mL)
6. waitThe solid was suspended in Et2O (10 mL) for 2 h
7. filtrationwas collected via suction filtration
8. customwas air-dried overnight

ORD record

ord-3d8596deca0a4b0cae4f70950a88aa5d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318758B2