Dichloromethane → HCID 67187943, compound

Participants

Reaction Steps

To a stirred solution of 3-(1-(2-chlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.1233 g, 285 μmol) in DCM was added DDQ (71 mg, 314 μmol) and the resulting dark-colored mixture was stirred at RT for 3 h. The reaction was quenched with NaHCO3(aq) and water (10 mL each) and the separated aqueous layer was extracted with 5% MeOH in DCM (3×6 mL). The combined organic layers were washed with, 1N NaOH(aq), brine, dried (Na2SO4), and concentrated to give the crude residue. Flash column chromatographic purification (5% MeOH in DCM) of the crude residue followed by washing the concentrated pure product fractions with ethyl acetate provided N-cyclopropyl-4-chloro-3-(2-oxo-1-o-tolyl-1,2-dihydroquinazolin-6-yl)benzamide as a white solid. MS m/e 430 (M+H)+.

Provenance & Evidence