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

HRID 584794Notes

Reaction equation

HRID 584794 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-66fc44af0fd4443db90a72745e973a42
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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