Pyridine → HCID 58166422, compound

Participants

Reaction Steps

4-Amino-1-(cyclopropylmethyl)-5-fluoropyrimidin-2(1H)-one (200 mg, 1.09 mmol) was dissolved in CH2Cl2 (0.90 mL) and pyridine (172.4 mg, 2.18 mmol) at room temperature and then was cooled to −20° C. Ethyl chloroformate (166 mg, 1.53 mmol) was then added to the reaction mixture dropwise, keeping the reaction temperature between −20 and −5° C. After the addition was complete, the reaction was allowed to warm slowly to room temperature and stirred for 2 h. The reaction mixture was filtered, and the solids were rinsed with EtOAc (15 mL×3). The filtrate was concentrated in vacuo, and purified by preparative thin layer chromatography, to afford ethyl 1-(cyclopropylmethyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate (70 mg, 30%) as a pale yellow solid: mp 90-92° C.; 1H NMR (400 MHz, methanol-d4) δ 8.20 (s, 1H), 4.26 (q, J=7.1 Hz, 2H), 3.70 (d, J=7.2 Hz, 2H), 1.24-1.36 (m, 4H), 0.65-0.57 (m, 2H), 0.46-0.39 (m, 2H); ESIMS m/z 256 ([M+H]+).

Provenance & Evidence