Acetic Acid → HCID 178437881, compound

HRID 2257017Notes

Reaction equation

HRID 2257017 reaction equation
[CH:1]1([N:6]2[C:10]([NH:11][C:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)=O)=[C:9]([C:25]#[N:26])[C:8]([CH2:27][CH3:28])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:29](C)[Na].OO.C(O)(=O)C>C(O)C.O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=4)=[N:26][C:25](=[O:29])[C:9]3=[C:8]([CH2:27][CH3:28])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide3×HCID 21830876HCID 21830876, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 178437881HCID 178437881, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

To a mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-[(3,4-dimethoxyphenylmethyl)carbonylamino]-1H-pyrazole (1.0 g, 2.7 mmol), ethanol (500 ml), and NaOCH3 (0.3 g) was added 30% H2O2 (4 ml). The reaction mixture was stirred at room temperature overnight, additional 30% H2O2 (3 equivalents) was added and the reaction mixture was refluxed on a steam bath for 1 hour. Starting material was still present so an additional 3 equivalents of 30% H2O2 was added and the reaction mixture was refluxed for 4 hours. The reaction mixture was stripped to dryness, treated with acetic acid and ethanol and again was stripped to dryness. The oily residue was dissolved in ethanol, water was added and the solution was cooled in an ice-bath. A solid formed which was collected by filtration and dried at 90° C. to afford 0.3 g (30%) of 1-cyclopentyl-3-ethyl-6-(3,4-dimethoxyphenylmethyl)-pyrazolo[3,4-d)pyrimidin-4-one, 1/10 hydrate, as a light yellow solid, m.p. 148°-149° C.

Workup

  1. temperaturethe reaction mixture was refluxed on a steam bath for 1 hour
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 4 hours
  4. temperaturethe solution was cooled in an ice-bath
  5. customA solid formed which
  6. filtrationwas collected by filtration
  7. customdried at 90° C.

Sources & evidence

ORD record
ord-6dad5c2409fb4674845c32fbe8c65f67
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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