Ethyl (3-chlorobenzoyl)acetate → 3-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872084Notes

Reaction equation

HRID 872084 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[C:5]([NH2:14])[NH:4][N:3]=1.[Cl: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>[Cl: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:18]4[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=4)=[CH:23][C:24](=[O:25])[NH:14][C:5]=23)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2757831Ethyl (3-chlorobenzoyl)acetateHCID 178434635HCID 178434635, compound

Product 1

HCID 1363939313-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneYield 41.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methyl-4-(4-chlorophenyl)-1H-pyrazol-5-amine (578 mg) and ethyl 3-(3-chlorophenyl)-3-oxopropanoate (728 mg) are stirred overnight in a pyridine (30 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 concentrated and then 424 mg of the target compound is yielded by column chromatography. 1H NMR (CDCl3, 300 MHz) δ 9.90 (br, 1H), 7.88 (m, 1H), 7.75 (m, 1H), 7.53 (m, 1H), 7.33 (m, 5H), 3.99 (br, 1H), 2.23 (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
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b0b960c08154c4ba7d433be0f3979fe
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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