반응식
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:17]1([C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)[CH:21]=[CH:20][N:19]=[CH:18]1>>[CH:1]1([N:6]2[C:10]3=[N:11][C:26]([C:25]4[CH:24]=[CH:23][C:22]([N:17]5[CH:21]=[CH:20][N:19]=[CH:18]5)=[CH:29][CH:28]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1참가 물질
반응 조건
- 온도
- 130 °C
실험 절차
A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.18 g, 5.32 mmol), 4-(1-imidazolyl)benzaldehyde (1.37 g) and xylenes (8 ml) was warmed to 130° C. for 30 minutes, then to 160° C. for three days. The reaction mixture was cooled, and the product was collected by filtration and washed with Et2O to afford 1.88 g of 1-cyclopentyl-3-ethyl-6-[4-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one as the 6,7-saturated derivative. This derivative was mixed with ethanol (300 ml) and 30% H2O2 (3.0 ml) and refluxed overnight. Additional 30% H2O2 (3 ml) was added and the mixture was refluxed for 8 hours. An additional 10 ml of 30% H2O2 was added and the mixture was refluxed overnight. Starting material was still present so an additional 10 ml of 30% H2O2 was added and the mixture was refluxed for 4 hours and then additional 30% H2O2 (10 ml) was added and the mixture was stirred for 1 hour, then was allowed to stand at room temperature overnight. The reaction mixture was stripped to a yellow liquid and purified by column chromatography on silica gel eluting with ethyl acetate (100%), then 5% methanol/ethyl acetate to afford 0.4 g of 1-cyclopentyl-3-ethyl-6-[4-(1-imidazolyl)phenyl]-pyrazolo[3,4-d]pyrimidin-4-one 1/2 hydrate, m.p. >300° C.
후처리
- temperatureThe reaction mixture was cooled
- filtrationthe product was collected by filtration
- washwashed with Et2O
출처 및 근거
- ORD 기록
- ord-07327be4e6924d88a6c7ad5e59a6443f
- 출처 데이터셋
- uspto-grants-1999_09
- 특허 번호
- US05958929
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