Tetrahydrofuran → HCID 58456407, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-propanoate (Example 79-1, 100 mg, 0.229 mmol) was taken up in THF (5 mL) and cooled to −78° C. Methylmagnesium bromide (3.0 M in Et2O, 305 μL, 0.916 mmol) was added, and the reaction was stirred at −78° C. for 90 min. It was then warmed to room temperature. After 1 h at room temperature, the reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Column chromatography on silica (20-100% ethyl acetate in hexanes) afforded 2-methyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]butan-2-ol (73 mg, 75%) as a white foam. MS ESI: [M+H]+ m/z 423.1. 1H NMR (600 MHz, DMSO-d6) δ 10.22 (s, 1H), 8.81 (d, J=4.8, 1H), 7.93 (s, 1H), 7.89 (s, 1H), 7.42 (s, 1H), 7.25 (d, J=4.8, 1H), 7.11 (s, 1H), 436 (s, 1H), 3.05-2.92 (m, 2H), 2.28 (s, 3H), 1.87-1.73 (m, 2H), 1.11 (s, 6H). rhSYK activity=+++

Provenance & Evidence