2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14460145, compound

Participants

Reaction Conditions

Reaction Steps

2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) (7.69 gm, 34 mmol) was added to a solution of 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-ethoxycarbonyl-1,2-dihydropyrimidine obtained in step (i) above (10.200 gm, 28 mmol) in toluene (200 ml). The red solution was then heated at 50° C. for 3 hours. The solution was cooled to room temperature, then passed through a silica gel plug which was washed with 10% EtOAc in hexane. The filtrate was concentrated to give an amber oil. The oil was purified by flash chromatography on Merck silica gel in 15% EtOAc in hexane. Fractions containing the desired product were pooled and concentrated to give a clear oil which solidified to afford the title compound as a white, crystalline solid (8.800 gm, 87%) (mp 97°-99° C.).

Provenance & Evidence