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

HRID 872096Notes

Reaction equation

HRID 872096 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[F:8][C:9]1[CH:10]=[C:11]([C:16](=O)[CH2:17][C:18](OCC)=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1>N1C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]([C:16]2[N:4]3[N:3]=[C:2]([CH3:1])[CH:6]=[C:5]3[NH:7][C:18](=[O:19])[CH:17]=2)[CH:12]=[C:13]([F:15])[CH:14]=1

Participants

4

Reactant 2

HCID 13550003Ethyl 3-(3,5-difluorophenyl)-3-oxopropanoateHCID 178418690HCID 178418690, compound

Product 1

HCID 1363939087-(3,5-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneYield 36.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methylpyrazol-5-amine (526 mg) and ethyl 3-(3,5-difluorophenyl)-3-oxopropanoate (879 g) are stirred overnight in a pyridine (30 mL) solvent at 85° 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 (521 mg).

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

Sources & evidence

ORD record
ord-c43e30d0267e47a992449c85afe83c5a
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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