2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67188551, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-(4-methoxybenzyl)-1-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)-N-cyclopropyl-N,4-dimethylbenzamide (0.445 g, 948 μmol) in TFA(4.00 ml) in a microwave reaction vessel was sealed and heated at 100° C. for 20 min under microwave irradiation. After cooling, the mixture was filtered through a short path of Celite and the filter cake was washed with EtOAc (3×10 mL). The mixture was concentrated and the crude product was taken up to a solution of DCM (5.00 ml), treated with DDQ (215 mg, 948 μmol) at 0° C. for 10 min then stirred at RT for 1 h. The reaction was quenched with NaHCO3(aq) and water (10 mL each) and the separated aqueous layer was extracted with DCM (5 mL×3). The combined organic phases were washed with 1N NaOH(aq), brine, dried (Na2SO4), and concentrated to give a crude residue. Flash column chromatographic purification (5% MeOH in DCM) of the residue provided the title compound N-cyclopropyl-N,4-dimethyl-3-(1-methyl-2-oxo-1,2-dihydroquinazolin-6-yl)benzamide as a pale tan solid. MS m/e 308 (M+H)+.

Provenance & Evidence