Sodium Hydroxide → (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanone

Participants

Reaction Steps

To a solution of (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol (Preparation 228, 11.4 g, 25 mmol) in CH2Cl2 (150 mL), Dess-Martin periodinane (15.9 g, 37 mmol) was added in portions. The reaction mixture was stirred at room temperature for 10 hours and then aqueous NaOH (30 mL) was added. The mixture was stirred for a further 0.5 hours. The mixture was then separated and the aqueous layer was exacted by CH2Cl2 (100 mL×2). The combined organic layers were concentrated and washed with ether to provide the title compound as a brown solid in 99% yield, 11 g.

Provenance & Evidence