Tetrabutylammonium Fluoride → 3-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Participants

Reaction Steps

A solution of 3-[2-{3-(tert-butyldimethylsilyloxy)cyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (570 mg) and 70% aqueous tetrabutylammonium fluoride (4.3 g) in tetrahydrofuran (10 ml) was stirred for overnight at room temperature. A reaction mixture was diluted with ethyl acetate (100 ml), which was washed in turn with water (50 ml×4) and saturated sodium chloride in water (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (40 ml) eluting in turn with 30%, 50% ethyl acetate in dichloromethane and ethyl acetate. Fractions containing desired product were concentrated under reduced pressure to give residue, which was recrystallized from ethanol to give 3-[2-(3-hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (430 mg).

Provenance & Evidence