Water → HCID 178437879, compound

HRID 2257021Notes

Reaction equation

HRID 2257021 reaction equation
[Na].[CH:2]1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9]([CH2:16][CH3:17])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O-])=O)=[CH:22][CH:21]=1.O>C(O)C>[CH:2]1([N:7]2[C:11]3=[N:12][C:27]([CH2:26][C:23]4[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=4)=[N:15][C:13](=[O:14])[C:10]3=[C:9]([CH2:16][CH3:17])[NH:8]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 4740745HCID 4740745, compoundHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437879HCID 178437879, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium spheres (207 mg) were dissolved in ethanol (15 ml) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.0 g) was added, followed by 4-methoxyphenylacetate (1.62 g, 9 mmol). The reaction mixture was refluxed for 16 hours, the solvent was stripped, water was added to the residue, and the product was collected by filtration and recrystallized from ether to afford 0.89 g of 1-cyclopentyl-3-ethyl-6-(4-methoxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 172°-173° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. filtrationthe product was collected by filtration
  3. customrecrystallized from ether

Sources & evidence

ORD record
ord-0bd764de46e2452cb85c22721ebd7077
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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