Water → Tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

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Reaction Steps

A mixture of tert-butyl 4-[6-[6-(6-vinylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (513 mg; 1.06 mmol), N-methylmorpholine-N-oxide monohydrate (744 mg, 6.35 mmol) and 2.5% solution of osmium tetroxide in tert-butanol (0.6 ml, 0.04764 mmol) in 20 ml of acetone and 2.5 ml of water was stirred at room temperature for 24 hours. The mixture was filtered, mixed with water and extracted with EtOAc. The organic extracts were washed with water, 5% aq. citric acid, sat. aq. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was triturated with ethyl ether, the precipitate was collected by filtration and washed with ethyl ether affording tert-butyl 4-(6-(6-(6-(1,2-dihydroxyethyl)pyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate (424 mg, 67%). MS (ESI) m/z: 519.3 [M+H]+

Provenance & Evidence