反应详情

A mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-[(4-pyridinylmethyl)carbonylamino]-1H-pyrazole (2.8 g, 8.6 mmol), ethanol (50 ml), NaOCH3 (1.0 g, 18 mmol) and 30% H2O2 (4.5 ml) was stirred at room temperature for 20 minutes, then was heated at reflux for 3.5 hours. Additional 30% H2O2 (3 ml) was added and the reaction mixture was heated at reflux for 2 more hours. The reaction mixture was concentrated in vacuo, the residue was partitioned between CHCl3 (100 ml) and 10% aqueous NaHCO (50 ml), and the organic layer was separated. The organic layer was concentrated in vacuo, and the residue was crystallized from cyclohexane and a solid was collected by filtration. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ether to 10% methanol/ether, followed by recrystallization from ether, to afford 420 mg of 1-cyclopentyl-3-ethyl-6-(4-pyridinylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 162°-164° C.

1. temperaturewas heated
2. temperatureat reflux for 3.5 hours
3. temperaturethe reaction mixture was heated
4. temperatureat reflux for 2 more hours
5. concentrationThe reaction mixture was concentrated in vacuo
6. customthe residue was partitioned between CHCl3 (100 ml) and 10% aqueous NaHCO (50 ml)
7. customthe organic layer was separated
8. concentrationThe organic layer was concentrated in vacuo
9. customthe residue was crystallized from cyclohexane
10. filtrationa solid was collected by filtration
11. concentrationThe filtrate was concentrated in vacuo
12. customthe residue was purified by column chromatography on silica gel eluting with ether to 10% methanol/ether
13. customfollowed by recrystallization from ether