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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanol (Preparation 194, 1820 mg, 4.5 mmol) in MeCN (45 mL) was added MnO2 (1960 mg, 22.5 mmol) portionwise and the resulting mixture stirred at 50° C. overnight. Another portion of MnO2 (1960 mg, 22.5 mmol) was added to the reaction and the mixture heated to reflux for 5 hr. After cooling to room temperature, the reaction mixture was filtered through a pad of arbocel, the filter cake rinsed with DCM (100 mL) and the resulting filtrate concentrated in vacuo. The resulting material was purified by column chromatography on silica gel (gradient of EtOAc:MeOH 100:0 to 90:10) to give the desired compound as a solid in 61% yield, 1120 mg.

Provenance & Evidence