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

HRID 487303Notes

Reaction equation

HRID 487303 reaction equation
[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

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 128666953-EthoxyisonicotinonitrileHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

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

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-6f95592b8ac6417c91a63d759fdccba3
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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