Acetic Acid → HCID 15838383, compound

Participants

Reaction Steps

To a solution of 1-cyclopentyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine (4.6 g, 0.016 mol) in sulfuric acid (60 ml) in an ice-bath was added dropwise 70% nitric acid (36.8 ml). The reaction mixture was warmed to room temperature, stirred for 30 minutes then heated on a steam bath for 3/4 hour. The reaction mixture was added to ice-water/50% sodium hydroxide and the pH was adjusted to 4-5 with acetic acid. The product was collected by filtration and washed with water. The solid residue was purified by preparative thin layer chromatography on silica eluting with ethyl acetate (100%) to afford, after recrystallization from ethyl acetate, 0.81 g (16%) of 1-cyclopentyl-3-nitro-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine, m.p. 239°-241° C. when dried for 16 hours at 110° C. in high vacuum.

Provenance & Evidence