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

HRID 54949

Reaktionsgleichung

Reaktionsgleichung von HRID 54949
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-433c0b0ad6fb44ebb147f39609782179
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624931

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