Trifluoroacetic acid → HCID 178510667, compound

Participants

Reaction Steps

To a solution of 1-cyclopentyl-3-cyano-6-(4-pyridyl)pyrazolo(3,4-d)pyrimidin-4-amine (0.61 g, 2.0 mmol) in 50% acetic acid (70 ml) at -5° to 0° C. was added 50% trifluoroacetic acid (10 ml) followed by sodium nitrite (2.8 g, 40.6 mmol) in water (15 ml). The reaction mixture was stirred at -5° to 0° C. for 1 hour, then at room temperature for 3 hours. The reaction mixture was cooled back to -5° to 0° C. and sodium nitrite (1.4 g, 20.3 mmol) in water (5 ml) was added. The reaction mixture was warmed to room temperature and stirred for 3 hours. The mixture was poured onto ice-water, concentrated ammonium hydroxide was added, followed by acetic acid to adjust the pH to 5. The product was collected by filtration, washed with water and recrystallized from ethanol to afford 0.48 g (79%) of 1-cyclopentyl-3-cyano-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one as a white fluffy powder, m.p. >300° C. when dried at 110° C. for 96 hours in high vacuum.

Provenance & Evidence