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

HRID 872085Notes

Reaction equation

HRID 872085 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][O:16][C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][C:25](OCC)=[O:26])[CH:20]=[CH:21][CH:22]=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:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH3:15])[CH:18]=4)=[CH:24][C:25](=[O:26])[NH:14][C:5]=23)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2759696Ethyl 3-(3-methoxyphenyl)-3-oxopropanoateHCID 178423836HCID 178423836, compound

Product 1

HCID 1364090773-(4-methylphenyl)-7-(3-methoxyphenyl)-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-methoxyphenyl)-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 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
  5. customthe target compound is yielded by column chromatography

Sources & evidence

ORD record
ord-2216046163e0473094b17b94538839bb
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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