Triethylamine → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-dimethylaminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Participants

Reaction Steps

To a solution of 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone (33 mg, 0.066 mmol) (INTERMEDIATE 73) in 1,2-dichloroethane (1.0 mL) at RT (under a nitrogen atmosphere) was added dimethylamine hydrochloride (11 mg, 0.132 mmol) followed by triethylamine (18 μL, 0.132 mmol). The reaction-mixture was stirred for 10 min then NaBH(OAc)3 (21 mg, 0.099 mmol) was added to the reaction. After 1.5 h the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution followed by brine, and dried over Na2SO4. The crude residue was purified by preparative thin layer chromatography using 5% MeOH in DCM as the eluent to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-dimethylaminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone (diastereomer A and diastereomer B).

Provenance & Evidence