Iodoethane → 9-Chloro-6-[cyclopropyl(ethoxy)methyl]-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

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Reaction Conditions

Reaction Steps

To a solution of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl](cyclopropyl)methanol (150 mg, 0.355 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (60% dispersion in mineral oil, 17 mg, 0.426 mmol) at 0° C. After the mixture was stirred at 0° C. for 0.5 hr, iodoethane (0.131 mL, 0.533 mmol) was added to the reaction mixture at 0° C. The mixture was stirred at room temperature for 2 hr. Saturated aqueous ammonium chloride was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture and recrystallization from isopropyl ether/n-hexane to give the title compound (73.1 mg, 0.154 mmol, 69%) as colorless crystals.

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