Hydrochloric Acid → HCID 67520919, compound

Participants

Reaction Steps

1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (1.93 g, 4.81 mmol) was dissolved in 20 mL of ethanol and treated with 1.6 mL of 3 M HCl in ethanol and the mixture was heated to reflux. After 2 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between 50 mL of CHCl3 and 25 mL of dilute NH4OH solution. The layers were separated and the aqueous portion was extracted with additional CHCl3 (12×20 mL). The combined organic portions were washed with 10 mL of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 25% CMA/CHCl3) gave 2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]ethanol (1.93 g) as a light-yellow powder.

Provenance & Evidence