Dimethylformamide → 1-Cyclopentyl-3-ethyl-6-(3-ethoxy-4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1736590노트

반응식

[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=O)[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([O:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1[C:26]#N)[CH3:18].[H-].[Na+].C[N:31](C=O)C>>[CH:1]1([N:6]2[C:10]3=[N:11][C:26]([C:25]4[CH:24]=[CH:23][N:22]=[CH:21][C:20]=4[O:19][CH2:17][CH3:18])=[N:14][C:12]([NH2:31])=[C:9]3[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 128666953-Ethoxyisonicotinonitrile

HCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

생성물 1

HCID 194328141-Cyclopentyl-3-ethyl-6-(3-ethoxy-4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine수율 44%

실험 절차

To a mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9.0 mmol), DMF (30 ml), and 3-ethoxy-4-cyanopyridine (1.47 g, 9.9 mmol) under argon was added sodium hydride (0.43 g, 10.8 mmol). The mixture was stirred at room temperature for 24 hours and the solvent was removed in vacuo. The residue was treated with water, acidified with acetic acid and a precipitate formed which was collected by filtration. The residue was purified by column chromatography on silica eluting with ether (100%) to acetone (100%) to afford 1.4 g (44%) of 1-cyclopentyl-3-ethyl-6-(3-ethoxy-4-pyridyl)pyrazolo[3,4-d]-pyrimidin-4-amine.

후처리

customthe solvent was removed in vacuo
additionThe residue was treated with water
customa precipitate formed which
filtrationwas collected by filtration
customThe residue was purified by column chromatography on silica eluting with ether (100%) to acetone (100%)

출처 및 근거

ORD 기록: ord-20eb174ae5b749808f4115a4a58f42d9
출처 데이터셋: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05541187

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