Acetic Anhydride → 4-Acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 54951Notes

Reaction equation

HRID 54951 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCCl>[C:30]([N:13]1[CH2:14][CH2:15][CH2:16][N:11]2[N:10]=[C:9]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:12]12)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 136087720HCID 136087720, compound

Product 1

HCID 199572914-Acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (100 mg), triethylamine (0.4 ml) and acetic anhydride (0.2 ml) in dry 1,2-dichloroethane (3 ml) was refluxed for 2 days. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in dichloromethane and the solution was washed with an aqueous saturated sodium bicarbonate solution and brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diisopropyl ether to give 4-acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (60 mg).

Workup

  1. temperaturewas refluxed for 2 days
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution was washed with an aqueous saturated sodium bicarbonate solution and brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel
  9. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a21526bd6cb9488cb0e02b2271a92a6f
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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