Acetic Acid → HCID 178437881, compound

Participants

Reaction Steps

To a mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-[(3,4-dimethoxyphenylmethyl)carbonylamino]-1H-pyrazole (1.0 g, 2.7 mmol), ethanol (500 ml), and NaOCH3 (0.3 g) was added 30% H2O2 (4 ml). The reaction mixture was stirred at room temperature overnight, additional 30% H2O2 (3 equivalents) was added and the reaction mixture was refluxed on a steam bath for 1 hour. Starting material was still present so an additional 3 equivalents of 30% H2O2 was added and the reaction mixture was refluxed for 4 hours. The reaction mixture was stripped to dryness, treated with acetic acid and ethanol and again was stripped to dryness. The oily residue was dissolved in ethanol, water was added and the solution was cooled in an ice-bath. A solid formed which was collected by filtration and dried at 90° C. to afford 0.3 g (30%) of 1-cyclopentyl-3-ethyl-6-(3,4-dimethoxyphenylmethyl)-pyrazolo[3,4-d)pyrimidin-4-one, 1/10 hydrate, as a light yellow solid, m.p. 148°-149° C.

Provenance & Evidence