Hydrogen Bromide → 4-Methoxybenzyl-[4-[2-piperidin-4-yl-5-(3-trifluoromethylphenyl)-3H-imidazol-4-yl]-pyrimidin-2-yl]amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-[5-[2-(4-methoxybenzylamino)-pyrimidin-4-yl]-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (1.0 g, 0.00156 mole) in methylene chloride (16 mL) under argon was slowly added 30% hydrogen bromide in acetic acid (16 mL). The mixture was stirred at 20° C. for 30 minutes and then diluted with diethyl ether (160 mL). The resulting mixture was stirred for I hour, filtered and solid washed with ether (10 mL). The resulting solid was dissolved in 10% aqueous sodium bicarbonate (40 mL) and methylene chloride (50 mL). The methylene chloride was separated and the aqueous layer washed with methylene chloride (25 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated to a foam (0.80 g). The solid was chromatographed on silica using methylene chloride/methanol/aqueous ammonium hydroxide (90:10:2) to give upon concentration of product containing fractions 180 mg of the title compound.

Provenance & Evidence