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Acetic Acid → 5-Chloro-6-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester

HRID 1851235
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HRID 1851235 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]2[C:13](Cl)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[C:11]([Cl:23])=[N:10][C:9]=12)=[O:4].C(O)(=O)C>CO.C1COCC1.[Zn].[Cu]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]2[CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[C:11]([Cl:23])=[N:10][C:9]=12)=[O:4]
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참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 867030485,7-Dichloro-6-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester

생성물 1

HCID 867030475-Chloro-6-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester수율 29.7%

시약·촉매·용매 3

HCID 10290809Zinc copper couple촉매HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

500 mg (1.4 mmol) 5,7-Dichloro-6-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester are dissolved in a mixture of 0.68 mL methanol and 3.9 mL THF. After addition of 0.16 mL acetic acid and 264 mg (2 mmol) zinc/copper pair, the mixture is vigorously stirred at rt over night. The reaction mixture is filtered via a glass microfibre filter and washed with plenty of methanol. The solvent has been removed and the residue purified by chromatography (silicagel, ethyl acetate/hexane). 134 mg (29.7%) of the desired product are obtained.

후처리

  1. filtrationThe reaction mixture is filtered via a glass microfibre
  2. filtrationfilter
  3. washwashed with plenty of methanol
  4. customThe solvent has been removed
  5. customthe residue purified by chromatography (silicagel, ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-fe637cf2adf84bc3b4204f64a1bbdc71
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957064B2

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