Tetrabutylammonium Fluoride → HCID 58456366, compound

Participants

Reaction Steps

To a solution of the product of Step 4 (327 mg, 0.517 mmol) in THF (3 mL) was added TBAF (1.0 M, 1.55 mL, 1.55 mmol), and the mixture stirred at room temperature for 2 weeks at which point LCMS showed complete conversion. The mixture was concentrated in vacuo, then the residue purified by chromatography on silica gel (60:40 to 0:100, hexanes:ethyl acetate) to provide 162 mg (0.411 mmol, 79%) of 2-methyl-2-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-1-ol as a white solid. MS APCI: [M+H]+ m/z 395.0. 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J=4.9 Hz, 1H); 8.07 (s, 1H); 7.85 (s, 1H); 7.63 (s, 1H); 7.49 (d, J=8.2 Hz, 1H); 7.37 (t, J=7.9 Hz, 1H); 7.26 (d, J=7.7 Hz, 1H); 7.07 (d, J=4.9 Hz, 1H); 3.79 (s, 2H); 1.48 (s, 6H). rhSYK activity=+++

Provenance & Evidence