Ethanol → 5-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-7-pyrimidinone

HRID 21950Notes

Reaction equation

HRID 21950 reaction equation
[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:10]([CH2:18][CH2:19][CH3:20])=[N:11][N:12]([CH3:17])[C:13]=1[C:14]([NH2:16])=[O:15])=O)[CH3:2].[OH-].[Na+].OO.C(O)C>O>[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]1[NH:16][C:14](=[O:15])[C:13]2[N:12]([CH3:17])[N:11]=[C:10]([CH2:18][CH2:19][CH3:20])[C:9]=2[N:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 8501354-(2-Ethoxybenzamido)-1-methyl-3-propylpyrazole-5-carboxamide

Product 1

HCID 1354014775-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-7-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-Ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide (223 g, 0.676 mol) was added portionwise to a solution of sodium hydroxide (54 g, 1.35 mol) and 30% hydrogen peroxide solution (224 ml) in water (2000 ml). Ethanol (700 ml) was added and the resulting mixture heated under reflux for 2.5 hours, cooled, then evaporated under vacuum. The resulting solid was treated with 2N hydrochloric acid (380 ml), with external cooling, and the mixture was extracted with dichloromethane (1×700 ml, 3×200 ml). The combined organic extracts were washed successively with saturated aqueous sodium carbonate solution (3×400 ml) and brine (300 ml), then dried (Na2SO4) and evaporated under vacuum.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturecooled
  4. customevaporated under vacuum
  5. additionThe resulting solid was treated with 2N hydrochloric acid (380 ml), with external cooling
  6. extractionthe mixture was extracted with dichloromethane (1×700 ml, 3×200 ml)
  7. washThe combined organic extracts were washed successively with saturated aqueous sodium carbonate solution (3×400 ml) and brine (300 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-d16e040e8e0b4967bf28214f5a764373
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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