Water → [2-(5-{1-[1-methyl-5-(methylsulfonyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

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Reaction Steps

A mixture of [2-(5-{1-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol (0.40 g), oxone (registered trade mark) (0.89 g), water (6 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (0.30 g, yield 70%) as a colorless amorphous solid from the fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 451 (MH+).

Provenance & Evidence