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Acetyl chloride → 3-(1-Acetyl-l,2-dihydro-2-methylpyridin-4-yl)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

HRID 1708023
Notes
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Reaction equation

HRID 1708023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:23](Cl)(=[O:25])[CH3:24].[CH3:27][Mg]Br.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:23]([N:20]1[CH:21]=[CH:22][C:17]([C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][N:10]3[CH:15]=[CH:14][CH:13]=[N:12][C:11]=23)=[CH:18][CH:19]1[CH3:27])(=[O:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 199572802-(4-Fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidineHCID 178418573HCID 178418573, compound

Product 1

HCID 199572613-(1-Acetyl-l,2-dihydro-2-methylpyridin-4-yl)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a solution of 2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (480 mg) in dry tetrahydrofuran (15 ml) was added acetyl chloride (0.89 ml) dropwise under ice cooling. The mixture was stirred at ambient temperature for 1 hour and to the mixture was added a solution of methyl magnesium bromide in tetrahydrofuran (1 mole solution, 12.42 ml) under ice cooling. The mixture was stirred at ambient temperature for 2 hours and to the mixture was added an aqueous saturated sodium bicarbonate solution. The separated oil was extracted with dichloromethane and the solution was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 3-(1-acetyl-1,2-dihydro-2-methylpyridin-4-Yl)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine (327 mg).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours and to the mixture
  2. extractionThe separated oil was extracted with dichloromethane
  3. washthe solution was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a46ca16b697b4ca98c900c54b355e2e4
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05356897

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes