Ethanol → HCID 178437867, compound

HRID 1600788Notes

Reaction equation

HRID 1600788 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-a224dbb6b9a74b41aa8affd83fdd2ea0
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

Loading…