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

HRID 327066Notes

Reaction equation

HRID 327066 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

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 702EthanolSolvent

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 (5ml). The mixture was heated under reflux for 38 hours and then evaporated under vacuum. The residue was suspended in water (20 ml), then the suspension acidified with 2N hydrochloric acid and extracted with dichloromethane (3×20 ml). The extracts were combined, dried (Na2SO4) and evaporated under vacuum. The resulting residue was chromatographed on silica gel (6 g), using a methanol in dichloromethane elution gradient (0-1% methanol), 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 (0-1% methanol)
  9. customto give an oil, successive trituration of which with ether

Sources & evidence

ORD record
ord-79ce69bb0936492c89339ad91611d9d1
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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