Sodium Thiosulfate → 1-[2-({3-[2-(1-Hydroxycyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}amino)pyrimidin-4-yl]ethane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(5-{3-[(4-ethenylpyrimidin-2-yl)amino]-5-methylphenyl}-1,3-thiazol-2-yl)cyclobutanol (200 mg, 0.55 mmol) in THF/water (3.6 mL/1.8 mL) were added osmium tetroxide (4% in water, 0.22 mL, 0.027 mmol) and NMO (77 mg, 0.66 mmol). The reaction mixture was heated to 50° C. overnight. The mixture was cooled to room temperature, treated with aq. Na2S2O3 solution, left to stir overnight, and then extracted with ethyl acetate (3×). The combined organics were washed with brine, dried (sodium sulfate), filtered, concentrated, and purified by column chromatography on silica to afford 1-[2-({3-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}amino)pyrimidin-4-yl]ethane-1,2-diol (47 mg, 0.12 mmol). MS ESI: [M+H]+ m/z 399.1. 1H NMR (500 MHz, DMSO-d6) δ 9.60 (s, 1H), 8.45 (d, J=5.1, 1H), 7.96 (s, 2H), 7.50 (s, 1H), 7.04 (s, 1H), 6.94 (d, J=4.9, 1H), 6.50 (s, 1H), 5.52 (s, 1H), 4.77 (m, 1H), 4.43 (m, 1H), 3.72 (m, 1H), 3.60 (m, 1H), 2.29 (s, 3H), 2.60-1.80 (m, 6H). rhSYK activity=+++

Provenance & Evidence