Dichloromethane methanol → 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide

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Reaction Steps

4-[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol (Step 1, Example 132, 300 mg, 0.663 mmol) was taken up in a 2:1 v/v CH2Cl2/MeOH mixture (6 mL) and magnesium monoperoxyphthalate hexahydrate (615 mg, 0.994 mmol) was added. The reaction was stirred at room temperature for 2 h, diluted with aqueous 10% Na2S2O3 and water and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Column chromatography on silica (gradient elution, 0 to 75% EtOAc in hexanes) afforded 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide (0.216 g, 0.446 mmol, 67% yield) as a yellow solid. MS ESI: [M+H]+ m/z 485.0.

Provenance & Evidence