HCID 57786383, compound → HCID 57785846, compound

Participants

Reaction Steps

Under nitrogen atmosphere, diethyl zinc (1 M solution in hexane, 0.860 mL, 0.860 mmol) was added to a solution of 1-[9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]but-3-en-1-ol (75.0 mg, 0.172 mmol) in dichloromethane (1.7 mL) at 0° C., and then diiodemethane (0.139 mL, 1.73 mmol) was added at 0° C. The resultant mixture was stirred at room temperature for 2 hr, diluted with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give a solid, which was recrystallized from ethyl acetate/hexane to afford the title compound as a colorless solid (17.5 mg, 00388 mmol, 23%).

Provenance & Evidence