Chlorophenyl isocyanate → HCID 58166395, compound

Participants

Reaction Steps

To a stirred solution of 4-amino-1-(cyclopropylmethyl)-5-fluoropyrimidin-2(1H)-one (150 mg, 0.819 mmol) in dry CH3CN (7.5 mL) at room temperature and under nitrogen was added 2-chlorophenylisocyanate (138.3 mg, 0.90 mmol). After stirring for 1 h, the crude reaction mixture was filtered, and the solids were rinsed with CH3CN (10 mL). The collected filtrate was then concentrated in vacuo and dried under high vacuum to afford 1-(2-chlorophenyl)-3-(1-(cyclopropylmethyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)urea (160 mg, 58%) as an off-white solid: mp 197-199° C.; 1H NMR (400 MHz, methanol-d4) δ 8.26 (d, J=6.0 Hz, 1H), 8.21 (dd, J=8.3, 1.5 Hz, 1H), 7.47 (dd, J=8.0, 1.4 Hz, 1H), 7.35-7.28 (m, 1H), 7.13 (td, J=7.8, 1.5 Hz, 1H), 3.74 (d, J=7.3 Hz, 2H), 1.32 (m, 1H), 0.69-0.58 (m, 2H), 0.50-0.38 (m, 2H); ESIMS m/z 337 ([M+H]+).

Provenance & Evidence