Guanidine Hydrochloride → 6-[4-(2-Amino-pyrimidin-4-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

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Reaction Steps

A suspension of 5-(4-chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (24 mg, 0.048 mmol) in MeOH (1 mL) is treated with guanidine hydrochloride (12 mg, 0.13 mmol) and NaOH (4 mg, 0.1 mmol) at 80° C. for 34 h. After cooling down to room temperature, the mixture is treated with saturated aqueus NH4Cl solution (2 mL) and extracted with EtOAc (3×2 mL). The organic layers are concentrated and purified by preparative thin layer chromatography (silica gel, 2.5% MeOH/CH2Cl2) to provide the titled compound 6-[4-(2-amino-pyrimidin-4-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as a white solid. 1H NMR (CDCl3) δ(ppm) 8.35(b, 1H), 8.34(s, 1H), 8.14 (d, 2H), 7.92 (d, 2H), 7.51 (t, 2H), 7.46 (d, 2H), 7.35(t, 1H), 7.32(d, 2H), 7.12(d, 2H), 7.03(d, 1H), 5.34(b, 2H); HPLC-MS calculated for C27H18ClN7O (M+H+): 492.1. Found: 492.2.

Provenance & Evidence