Tetrabutylammonium Fluoride → 2-[5-(3-Ethynyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-2-ol

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Reaction Steps

To a solution of the product of Step 2 (35 mg, 0.073 mmol) in THF (1.0 mL) was added TBAF (1.0 M in THF, 0.44 mL, 0.44 mmol) and the mixture was stirred at room temperature for 90 minutes. The mixture was concentrated in vacuo, then purified by chromatography on silica gel (80:20 to 30:70, hexanes:ethyl acetate) to provide 22 mg (0.054 mmol, 74%) of 2-[5-(3-ethynyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-2-ol as a white solid. MS ESI: [M+H]+ m/z 405.1. 1H NMR (400 MHz, CDCl3): δ 8.68 (d, J=4.9 Hz, 1H); 8.06 (s, 1H); 7.88 (s, 1H); 7.69-7.59 (m, 2H); 7.38 (s, 1H); 7.09 (d, J=4.9 Hz, 1H); 3.20 (s, 1H); 2.05 (s, 1H); 1.73 (s, 6H). rhSYK activity=+++

Provenance & Evidence