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

Reaktionsgleichung

[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

Komponenten

Edukt 3

HCID 702Ethanol

HCID 14797Potassium Hydroxide

HCID 22249848Ethyl 7-cyano-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

Produkt 1

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

Versuchsvorschrift

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).