Ethyl isocyanate → HCID 10270050, compound

Participants

Reaction Steps

To a solution of 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (2.92 g, 10 mmol) in THF (30 mL) was added 95% sodium hydride (0.30 g, 12 mmol). After gas evolution ceased, ethyl isocyanate (0.44 mL, 12 mmol) was added via syringe. The reaction mixture was stirred for 0.5 h, quenched with water and extracted twice with EtOAc. The combined extracts were washed with 0.5 N aqueous NaOH, with water and with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography (25% to 35% EtOAc/hexane) to give, after evaporation of solvent, 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl amide as a colorless solid (2.91 g; 80%): 1H NMR (CDCl3, 400 MHz) δ 8.65 (t, 3H, J=5.3 Hz), 7.91 (s, 1H), 7.39 (m, 1H), 7.35 (m, 1H), 7.21 (m, 1H), 7.15 (d, 1H, J=7.9 Hz), 6.24 (s, 1H), 3.25 (m, 2H), 2.10 (s, 3H), 1.10 (t, 3H, J=7.0 Hz); LC/MS (ES+) 363 (M+H+).

Provenance & Evidence