Ethyl chloroformate → HCID 9947173, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (0.29 g, 1 mmol) in THF (5 mL) chilled to −78° C. was added LDA (0.55 mL, 1.1 mmol, 2.0 M in THF). The resulting yellow suspension was stirred for 0.5 h, warmed to −20° C. for 0.5 h and recooled to −78° C.; then ethyl chloroformate (0.14 mL, 1.5 mmol) was added via syringe. The reaction mixture was stirred for 20 min, warmed to room temperature and quenched with EtOAc. This mixture was washed with aqueous NaHCO3 solution and with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography (10% to 30% EtOAc/hexanes) to give, after evaporation of solvent, 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl ester as a colorless solid (0.29 g; 80%): 1H NMR (CDCl3, 400 MHz) δ 7.48 (m, 2H), 7.28 (m, 2H), 5.87 (s, 1H), 4.33 (m, 2H), 2.22 (s, 3H), 1.33 (t, 3H, J=7.0 Hz); LC/MS (ES+) 364 (M+H+).

Provenance & Evidence