Acetic Acid → 1H-Pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Steps

3-Iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.00 g, 5.81 mmol), 1-methyl-4-piperidone (2.14 mL, 17.42 mmol), sodium triacetoxyborohydride (2.45 g, 11.62 mmol) and glacial acetic acid (1.05 g, 17.42 mmol) were mixed with 1,2-dichloroethane (75 mL). The reaction mixture was stirred at room temperature for 6 hours and saturated sodium bicarbonate solution was added to adjust the pH to about 9. The solid was collected by filtration to give 3-Iodo-1-[1-(1-methylpiperidin-4-yl)]-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.39 g, 93%). 1H NMR (DMSO-d6) δ 1.52 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 2.05 (m, 4H), 2.24 (s, 3H), 2.28 (m, 3H), 2.91 (m, 2H), 3.00 (m, 2H), 4.55 (m, 1H), 8.18 (s, 1H).

Provenance & Evidence