Ethyl isocyanate → HCID 58138376, compound

Participants

Reaction Steps

To a suspension of 1-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-3-(2-methoxybenzyl)urea (as prepared in U.S. Patent Appl. Publ. 2010022538; 0.25 g, 0.855 mmol) in dry THF (5 mL) was added ethyl isocyanate (0.074 mL, 0.941 mmol), and the mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo, and the solid residue was suspended in Et2O (10 mL). The suspension was suction filtered and washed with Et2O (2×10 mL). The resulting solid was dried in vacuo to yield N-ethyl-5-fluoro-4-(3-(2-methoxybenzyl)ureido)-2-oxopyrimidine-1(2H)-carboxamide (0.150 g, 48%) as a white solid: mp 248-250° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.56 (s, 1H), 9.92 (s, 1H), 9.68 (s, 1H), 8.55 (d, J=6.6 Hz, 1H), 7.33-7.20 (m, 2H), 7.02 (d, J=7.9 Hz, 1H), 6.91 (dd, J=7.9, 6.9 Hz, 1H), 4.41 (d, J=6.0 Hz, 2H), 3.88 (s, 3H), 3.38-3.24 (m, 2H), 1.14 (t, J=7.2 Hz, 3H). ESIMS m/z 362 ([M−H]−).

Provenance & Evidence