Ethyl 3-(3-methylphenyl)-3-oxopropanoate → 3-(4-methylphenyl)-7-(3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872108Notes

Reaction equation

HRID 872108 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[C:5]([NH2:14])[NH:4][N:3]=1.[CH3:15][C:16]1[CH:17]=[C:18]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])[CH:19]=[CH:20][CH:21]=1>N1C=CC=CC=1>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]3[C:22]([C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([CH3:15])[CH:17]=4)=[CH:23][C:24](=[O:25])[NH:14][C:5]=23)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2760277Ethyl 3-(3-methylphenyl)-3-oxopropanoateHCID 178423836HCID 178423836, compound

Product 1

HCID 1363939043-(4-methylphenyl)-7-(3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methyl-4-(4-methylphenyl)-1H-pyrazol-5-amine and ethyl 3-(3-methylphenyl)-3-oxopropanoate 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 purified by column chromatography to yield the target compound.

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
  5. custompurified by column chromatography
  6. customto yield the target compound

Sources & evidence

ORD record
ord-53f7821f15b948d8a57669f55007223b
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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