Sodium Bicarbonate → 2-(4-{[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]methyl}phenyl)-3-phenyl-1,6-naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-{1-[4-(5-methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (50 mg, 0.092 mmol) and pyridine hydrochloride 9500 mg, 4.35 mmol) was heated at 150° C. for 10 minutes. The cooled mixture was diluted with water and made neutral with sodium bicarbonate solution. The white solid was collected by filtration, dried, and then digested in acetonitrile with a little methanol. Upon cooling the pure product was isolated by filtration. 1H-NMR (500 MHz, DMSO-d6): δ 11.60 (1H, br s), 8.38 (1H, s), 8.15 (1H, s), 8.07 (1H, s), 7.50 (1H, d, J=7.3 Hz), 7.31-7.60 (5H, m), 7.24-7.28 (4H, m), 6.69 (1H, d, J=7.3 Hz), 4.57 (1H, m), 3.53 (2H, s), 2.91 (2H, m), 2.11-2.17 (4H, m), 1.80-1.87 (2H, m). m/e (m+1): 529.3.

Provenance & Evidence