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 hydrochloride (0.68 g, 1.26 mmol) and LiOH (69 mg, 1.64 mmol) in THF (15 mL) and water (5 mL) was stirred for 6 h at 50° C. The reaction was extracted with DCM. The combined organic phases were dried over MgSO4 and evaporated down to give the title compound as a tan solid, (0.55 g, 98% yield). 1H NMR (400 MHz, d6-DMSO): δ 9.73 (s, 1H), 8.82 (d, J=6.7 Hz, 1H), 8.60 (d, J=8.9 Hz, 1H), 8.42 (s, 1H), 8.29 (d, J=5.3 Hz, 1H), 8.24 (s, 1H), 7.76 (d, J=7.7 Hz, 1H), 7.61 (s, 1H), 7.35-7.44 (m, 3H), 7.10-7.19 (m, 2H), 6.83 (s, 1H), 6.69-6.73 (m, 2H), 6.58 (d, J=5.3 Hz, 1H), 5.30 (bs, 2H) ppm. ES-LC/MS m/z=446 [M+H]+.

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