Acetone → racemic 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexane-1,2-diol

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Reaction Steps

Osmium tetroxide (2.08 mL, 0.34 mmol) and 4-methylmorpholine N-oxide (398 mg, 3.4 mmol) were added to a flask containing racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (339 mg, 0.85 mmol) dissolved in acetone (7.5 mL) and water (0.94 mL). The suspension was stirred for 2.5 hours at room temperature. The mixture was diluted with saturated aqueous sodium thiosulfate and stirred for 15 minutes at room temperature. The mixture was extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford racemic 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexane-1,2-diol. MS ESI calcd. for C21H23F3N5O2 [M+H]+ 434. found 434.

Provenance & Evidence