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

HRID 487303노트

반응식

HRID 487303 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

5

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 128666953-EthoxyisonicotinonitrileHCID 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

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

출처 및 근거

ORD 기록
ord-6f95592b8ac6417c91a63d759fdccba3
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294612

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