Ethyl benzoylacetate → 3-(4-methoxyphenyl)-7-phenyl-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872091Notes

Reaction equation

HRID 872091 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[C:5]([NH2:15])[NH:4][N:3]=1.[C:16]1([C:22](=O)[CH2:23][C:24](OCC)=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]3[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:23][C:24](=[O:25])[NH:15][C:5]=23)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 178488690HCID 178488690, compound

Product 1

HCID 1363939333-(4-methoxyphenyl)-7-phenyl-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneYield 82.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methyl-4-(4-methoxyphenyl)-1H-pyrazol-5-amine (200 mg) and ethyl 3-phenyl-3-oxopropanoate (227 mg) are stirred overnight in a pyridine (10 mL) solvent at 95° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and 270 mg of the target compound is yielded by column chromatography.

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure

Sources & evidence

ORD record
ord-ca74bed193f4480aa65cddcab5791a09
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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