Thionyl Chloride → 5-(chloromethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

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Reaction Steps

To a solution of thionyl chloride (1.46 mL, 20.0 mmol) was added [1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (0.609 g, 2.0 mmol) slowly. The mixture was stirred at room temperature for 30 min and then was concentrated on rotavap under vacuum. The residue was twice taken up in DCM (5 mL) and concentrated on rotavap to afford the title compound 0.386 g (60%). LC-MS m/z 319 (M+H)+ [molecular ion of the compound with methoxy from LC-MS solvent methanol where OMe substituted chloro group of the original product].

Provenance & Evidence