Sodium Hydroxide → HCID 11612433, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-N-dimethylaminomethylene-benzamide (10 mg, 0.02 mmol) in acetic acid (200 μL) is added a mixture of NH2OH.HCl (5 mg, 0.072 mmol) in NaOH (1M, 50 μL, 0.05 mmol)). The mixture is stirred at 90° C. for 1 h. and cooled down to room temperature. Solvent is removed under vacuum and the residue is treated with saturated aqueous NaHCO3 solution (1 mL) and extracted with EtOAc (3×2 mL). The organic layers are combined and concentrated. The residue is purified by preparative thin layer chromatography (silica gel, 30% EtOAc/hex) to provide the titled compound 5-(4-chloro-phenyl)-6-(4-[1,2,4]oxadiazol-5-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid (8 mg, 85%). 1H NMR (CDCl3) δ(ppm) 8.50(s, 1H), 8.35(s, 1H), 8.12(d, 2H), 8.06(d, 2H), 7.48-7.54 (m, 4H), 7.37(t, 1H), 7.34(d, 2H), 7.11(d, 2H); HPLC-MS calculated for C25H16ClN6O2 (M+H+): 467.1. Found: 467.1.

Provenance & Evidence