Potassium Carbonate → HCID 69192521, compound

Participants

Reaction Steps

Solid potassium carbonate (2.68 g, 19.4 mmol) was added to a solution of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate (3.50 g, 12.9 mmol) in methanol (65 mL) at room temperature. The mixture was stirred for 3 hours, then the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (150 mL) and water (75 mL). The organic layer was washed with brine (75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown semi-solid that was triturated with dichloromethane and isolated by filtration to afford 0.48 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-50% CMA in chloroform) to provide an additional 0.67 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol.

Provenance & Evidence