Hydrogen Peroxide → HCID 178517636, compound

HRID 2257016Notes

Reaction equation

HRID 2257016 reaction equation
[CH:1]1([N:6]2[C:10]([NH:11][C:12]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=O)=[C:9]([C:21]#[N:22])[C:8]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:30]O.[OH-].[Na+]>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][CH:18]=[CH:17][CH:16]=4)=[N:22][C:21](=[O:30])[C:9]3=[C:8]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 218308801-cyclopentyl-3-phenylmethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazole

Product 1

HCID 178517636HCID 178517636, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To an ice-cooled solution of 1-cyclopentyl-3-phenylmethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazole (1.1 g, 2.8 mmol) in ethanol (30 ml) was added 30% H2O2 (2.5 ml), followed by NaOH (100 mg) dissolved in water (5 ml). The reaction mixture was stirred a such for 1 hour, then at room temperature for 1 hour, then it was heated on a steam bath for 3.5 hours and finally it was stirred at room temperature overnight. The reaction mixture was concentrated to dryness, and partitioned between water (25 ml) and CHCl3 (50 ml). The organic layer was separated, and concentrated in vacuo and the oily residue was crystallized from isopropanol to afford 234 mg (22%) of 1-cyclopentyl-3-phenylmethyl-6-(phenylmethyl)-pyrazolo[3,4-d]pyrimidin-4-one, as a white solid, m.p. 204°-206° C.

Workup

  1. waitat room temperature for 1 hour
  2. temperatureit was heated on a steam bath for 3.5 hours
  3. stirringfinally it was stirred at room temperature overnight
  4. concentrationThe reaction mixture was concentrated to dryness
  5. custompartitioned between water (25 ml) and CHCl3 (50 ml)
  6. customThe organic layer was separated
  7. concentrationconcentrated in vacuo
  8. customthe oily residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-884129ba957c48ec8a319debf37fcd53
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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