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

Participants

Reaction Steps

3-Iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.5 g, 1.45 mmol), formaldehyde (30% in water, 0.16 mL, 1.60 mmol) and sodium triacetoxyborohydride (0.43 g, 2.03 mmol) was mixed in dichloroethane (5 mL). After 4 hours, saturated sodium bicarbonate was added followed by sodium hydroxide (1.0N) to bring the pH to 10. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give 3-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.275 g, 53%). 1H NMR (DMSO-d6) δ 1.85 (m, 2H), 2.09 (m, 4H), 2.22 (s, 3H), 2.88 (m, 2H), 4.75 (m, 1H), 8.19 (s, 1H), 8.32 (s, 1H).

Provenance & Evidence