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

HRID 487303

Reaktionsgleichung

Reaktionsgleichung von HRID 487303
[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

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-6f95592b8ac6417c91a63d759fdccba3
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294612

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