Formaldehyde → 3-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

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Reaction Steps

To a mixture of 3-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride (0.5 g, 0.0012 mol) and sodium triacetoxyborohydride (0.36 g, 0.00168 mol) in dichloroethane (40 mL) was added formaldehyde solution (37% in water, 0.037 mL, 0.00132 mol) at room temperature. The mixture was stirred at room temperature under an atmosphere of nitrogen for 4 hours. A 5 N aqueous solution of sodium hydroxide (2 mL) was added to the mixture. The solvent was removed under the reduced pressure. The residue was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with water, and brine, and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure to leave solid. The solid was resubjected to the same reaction and work-up conditions as above to yield 3-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.3 g, 0.00084 mol). TLC (methanol/dichloromethane=10: 90) Rf 0.63 MS: MH+ 359

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