Ethanol → 3-Mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6,7-dicarboxylic acid

HRID 890179Notes

Reaction equation

HRID 890179 reaction equation
[OH-:1].[K+].C(C1[N:10]2[N:11]=[C:12]([CH3:23])[C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[C:9]2[N:8]=[C:7]([CH3:24])[C:6]=1[C:25]([O:27]CC)=[O:26])#N.[CH2:30]([OH:32])[CH3:31]>>[C:15]1([CH3:22])[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:14]=1[C:13]1[C:12]([CH3:23])=[N:11][N:10]2[C:31]([C:30]([OH:1])=[O:32])=[C:6]([C:25]([OH:27])=[O:26])[C:7]([CH3:24])=[N:8][C:9]=12

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22249848Ethyl 7-cyano-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

Product 1

HCID 222495723-Mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6,7-dicarboxylic acid

Procedure

Potassium hydroxide (441 mg, 11.04 mmol) was added to a solution of ethyl 7-cyano-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate (800 mg, 2.21 mmol) in ethanol (15 mL), followed by heating under reflux for two hours. The reaction mixture was evaporated, water was added. Under ice-cooling, 2N hydrochloric acid was added to adjust the pH of the mixture to pH 1. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to give the title compound (780 mg).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for two hours
  3. customThe reaction mixture was evaporated
  4. additionwater was added
  5. temperatureUnder ice-cooling
  6. addition2N hydrochloric acid was added
  7. extractionThe mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-c6420baad1e243e88f195205f010029f
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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