Acetic Acid → HCID 22347030, compound

Participants

Reaction Steps

3-(4-phenoxyphenyl)-1-(4-piperidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Compound 2) (221 mg, 0.572 mmol), 1-isopropyl-4-piperidone(89 mg, 0.63 mmol), sodium triacetoxyborohydride (182 mg, 0.86 mmol) and glacial acetic acid(40 ul, 0.63 mmol) were mixed with 3 ml of 1,2-dichloroethane. After stirring at room temperature overnight, 2 ml of water was added followed by solid sodium bicarbonate until PH reached about 8. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed, dried and evaporated. The residue was purified by flash column chromatography to give 132 mg of 1-[1-(1-isopropyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO) 0.99(d, J=6.54 Hz, 6H), 1.42(m, 2H), 1.72(d, J=11.41 Hz, 2H), 1.88(d, J=9.61 Hz, 2H), 2.14(s, 3H), 2.16(m, 6H), 2.66(m, 2H), 2.83(d,J=10.98 Hz, 2H), 2.98(d,J=8.25 Hz, 2H), 4.62(m, 1H), 7.16(m, 5H), 7.44(m, 2H), 7.67(d, J=8.69 Hz, 2H), 8.23(s, 1H); LC/MS (MH+=512)

Provenance & Evidence