Ethanol → HCID 178437867, compound

HRID 2257013Notes

Reaction equation

HRID 2257013 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][CH3:24])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([OH:27])C.OO.[OH-].[Na+]>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:27])[C:9]3=[C:8]([CH2:23][CH3:24])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 15871270HCID 15871270, compound

Product 1

HCID 178437867HCID 178437867, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazole (2.4 g, 7.4 mmol), ethanol (100 ml), 30% H2O2 (4.5 ml, 40 mmol), NaOH (0.3 g, 7.5 mmol) and water (10 ml) was stirred at room temperature for 1 hour, then at reflux for 1 hour. Additional 30% H2O2 (2.5 ml) was added and the mixture was refluxed for another 1 hour. The solvent was concentrated in vacuo, the residue was treated with water (25 ml) and acetic acid (3 ml) and the yellow precipitate which formed was collected by filtration, washed with water and recrystallized from isopropanol to afford 0.79 g of 1-cyclopentyl-3-ethyl-6-(phenylmethyl)-pyrazolo[3,4-d]pyrimdin-4-one, as orange needles, m.p. 175°-176° C.

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturethe mixture was refluxed for another 1 hour
  3. concentrationThe solvent was concentrated in vacuo
  4. additionthe residue was treated with water (25 ml) and acetic acid (3 ml)
  5. customthe yellow precipitate which formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-8270224c14a9489b935a6d3780a3191a
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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