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

HRID 1708023

반응식

HRID 1708023 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a46ca16b697b4ca98c900c54b355e2e4
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356897

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