Dimethylformamide → 1-Cyclopentyl-3-ethyl-6-[2-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine

HRID 619175Notes

Reaction equation

HRID 619175 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:14]1([N:19]2[C:23](N)=[C:22]([C:25]([NH2:27])=O)[C:21]([CH2:28][CH3:29])=[N:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C[N:31](C=O)C.[H-].[Na+]>C(O)(=O)C>[CH:14]1([N:19]2[C:23]3=[N:9][C:8]([C:7]4[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=4[N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[N:27][C:25]([NH2:31])=[C:22]3[C:21]([CH2:28][CH3:29])=[N:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1902752-(1H-imidazol-1-yl)benzonitrileHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 867523641-Cyclopentyl-3-ethyl-6-[2-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-(1-imidazolyl)benzonitrile (3.14 g), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.75 g, 16.59 mmol) and DMF (75 ml) was added 60% NaH (0.78 g, 60% dispersion in mineral oil). The reaction mixture was stirred at room temperature overnight, poured into ice/water (600 ml) and treated with acetic acid until a pH of 7 was obtained. The product was collected by filtration, and recrystallized from EtOAc/hexane to afford 2.82 g of 1-cyclopentyl-3-ethyl-6-[2-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine.1/4 hydrate.

Workup

  1. customwas obtained
  2. filtrationThe product was collected by filtration
  3. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-3bc31b21a8de4b26b58cc41aa38155c2
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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