Hydrogen Peroxide → HCID 178437884, compound

HRID 1600791Notes

Reaction equation

HRID 1600791 reaction equation
[CH:1]1([N:6]2[C:10]([NH:11][C:12]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=O)=[C:9]([C:21]#[N:22])[C:8]([CH2:23][CH3:24])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:25](C)[Na].OO>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:14][C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:22][C:21](=[O:25])[C:9]3=[C:8]([CH2:23][CH3:24])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 218308811-cyclopentyl-3-ethyl-4-cyano-5-[(4-pyridinylmethyl)carbonylamino]-1H-pyrazoleHCID 178418582HCID 178418582, compound

Product 1

HCID 178437884HCID 178437884, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-[(4-pyridinylmethyl)carbonylamino]-1H-pyrazole (2.8 g, 8.6 mmol), ethanol (50 ml), NaOCH3 (1.0 g, 18 mmol) and 30% H2O2 (4.5 ml) was stirred at room temperature for 20 minutes, then was heated at reflux for 3.5 hours. Additional 30% H2O2 (3 ml) was added and the reaction mixture was heated at reflux for 2 more hours. The reaction mixture was concentrated in vacuo, the residue was partitioned between CHCl3 (100 ml) and 10% aqueous NaHCO (50 ml), and the organic layer was separated. The organic layer was concentrated in vacuo, and the residue was crystallized from cyclohexane and a solid was collected by filtration. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ether to 10% methanol/ether, followed by recrystallization from ether, to afford 420 mg of 1-cyclopentyl-3-ethyl-6-(4-pyridinylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 162-164° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 2 more hours
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe residue was partitioned between CHCl3 (100 ml) and 10% aqueous NaHCO (50 ml)
  7. customthe organic layer was separated
  8. concentrationThe organic layer was concentrated in vacuo
  9. customthe residue was crystallized from cyclohexane
  10. filtrationa solid was collected by filtration
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe residue was purified by column chromatography on silica gel eluting with ether to 10% methanol/ether
  13. customfollowed by recrystallization from ether

Sources & evidence

ORD record
ord-4b386577d3e34d98bcffaa6087e161e1
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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