Lithium Hydroxide → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamine

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A solution of 2,2,2-trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide (0.89 g, 0.002 mols) and 1M LiOH (8.22 mL, 0.008 mols) in 10:1 THF:water (20 mL) was heated at 60° C. for 5 h. The reaction was washed with brine (25 mL), organic layer separated, aqueous layer extracted with EtOAc (25 mL), organic layers combined, filtered through a cotton plug, and solvent removed by rotary evaporation. The crude product was purified by column chromatography (5%-75% EtOAc in hexanes then 100% EtOAc) to provide the aniline (0.70 g, 96%) as a pale yellow foam. ES-LC/MS m/z=446 [M+H]+.

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