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

HRID 872086Notes

Reaction equation

HRID 872086 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]=[CH:13][C:14]=1[F:15]>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]=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 2

HCID 2758339Ethyl 3-(3,4-difluorophenyl)-3-oxopropanoateHCID 178418690HCID 178418690, compound

Product 1

HCID 1363939327-(3,4-Difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methylpyrazol-5-amine (670 mg) and ethyl 3-(3,4-difluorophenyl)-3-oxopropanoate (1.12 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 the target compound (821 mg) is yielded by column chromatography. 1H NMR (CDCl3, 300 MHz) δ 10.80 (br, 1H), 8.01 (m, 1H), 7.54 (m, 1H), 7.30 (m, 1H), 6.45 (s, 1H), 5.88 (s, 1H), 2.31 (s, 3H).

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-9a3e48c4bd104e55b5d88108ecda335e
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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