Hydrochloric Acid → 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoate (125 mg, 0.302 mmol) in THF (5.0 mL), methanol (1.0 mL), and water (1.0 mL) was diluted with sodium hydroxide (1.0 M in water, 1.0 mL, 1.0 mmol). The reaction mixture was stirred and heated to 50° C. for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with hydrochloric acid (1.0 M in water, 1.0 mL, 1.0 mmol) while stirring. The resulting suspension was diluted with ethyl acetate (100 mL) and brine (10 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford 4-(1-(4-(3-methyl-5-(pyrimidin-2-ylamino)phenyl)-1H-pyrazol-1-yl)ethyl)benzoic acid. The material was used without purification in the subsequent step. MS ESI calcd. for C23H22N5O2 [M+H]+ 400. found 400.

Provenance & Evidence