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Hydrogen Peroxide → 1-Methyl-5-(2-propoxyphenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

HRID 1532110
Notes
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Reaction equation

HRID 1532110 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][CH2:20][CH3:21])[C:4]([CH2:23][CH2:24][CH3:25])=[N:3]1.OO.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[CH3:1][N:2]1[C:6]2[C:7](=[O:8])[NH:9][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][CH2:20][CH3:21])=[N:10][C:5]=2[C:4]([CH2:23][CH2:24][CH3:25])=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 113937971-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide

Product 1

HCID 1357385471-Methyl-5-(2-propoxyphenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide (0.34 g, 0.99 mmol) was added to a stirred mixture of 30% hydrogen peroxide solution (1.0 ml), potassium carbonate (0.54 g, 3.92 mmol), water (10 ml) and ethanol (5 ml). The mixture was heated under reflux for 38 hours and then evaporated under vacuum. The residue was suspended in water (20 ml), then the mixture acidified with 2N hydrochloric acid and extracted with dichloromethane (3×20 ml). The extracts are combined, dried (Na2SO4) and evaporated under vacuum. The resulting residue was chromatographed on silica gel (6 g), using a methanol in dichloromethane elution gradient (0.0-1.0%), to give an oil, successive trituration of which with ether gave the required product as a white solid (0.19 g, 59%), m.p. 111-114° C. Found: C, 66.26; H, 6.92; N, 17.15. C18H22N4O2 requires C, 66.23; H, 6.80; N, 17.17%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 38 hours
  3. customevaporated under vacuum
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum
  7. customThe resulting residue was chromatographed on silica gel (6 g)
  8. washa methanol in dichloromethane elution gradient (0.0-1.0%)
  9. customto give an oil, successive trituration of which with ether

Sources & evidence

ORD record
ord-2ed865e76ac0452e9cd897e01311ff65
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06200980B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes