Hydrochloric Acid → HCID 57786045, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 0.10 mL, 0.10 mmol) was added dropwise to a stirred solution of 9-chloro-1-(2-cyclopropyl-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (294 mg, 0.770 mmol) and trimethyl(trifluoromethyl)silane (219 mg, 1.54 mmol) in tetrahydrofuran (3.0 mL) at 0° C., and the mixture was stirred at 0° C. for 40 min. 1N hydrochloric acid (3.0 mL) was added to the mixture at 0° C., and the mixture was stirred at 0° C. for 30 min. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (308 mg, 0.682 mmol, 89%).

Provenance & Evidence