Toluene → HCID 57964978, compound

Participants

Reaction Steps

4-(tert-Butoxycarbonyl-hydrazino)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 15; 315 mg, 1 mmol) and diisopropylethylamine (2 mmol) were added to a solution of 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA; 200 mg, 1 mmol) in tetrahydrofuran (3 mL). The mixture was warmed to room temperature, heated to reflux for 3 h, and then stirred overnight. The mixture was heated to reflux for a further 2 h and then cooled. Brine was added and the mixture was extracted three times with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered and evaporated to give a yellow foam. Toluene was added and the mixture was heated at 110° C. for 2 h. The mixture was cooled and purified by column chromatography (50% ethyl acetate/hexanes) to give 4-(6-amino-4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (315 mg, 69%) as a white powder.

Provenance & Evidence