Potassium Hydroxide → (5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanol

Participants

Reaction Steps

A mixture of 7H-pyrrolo[2,3-d]pyrimidine (Preparation 202, 953 mg, 8.0 mmol), 5-[(diphenylmethylene)amino]nicotinaldehyde (Preparation 106, 3340 mg, 11.7 mmol) and KOH (1350 mg, 24 mmol) in MeOH (16 mL) was stirred for 16 hours at room temperature. The reaction was neutralized with saturated aqueous ammonium chloride solution and the mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to obtain a crude residue. The crude material was purified by column chromatography on silica gel (EtOAc:MeOH=100:0 to 80:20,) to give the desired compound as a solid in 62% yield, 2003 mg.

Provenance & Evidence