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2,2,2-Trifluoroethanol → 4-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acid methyl ester

HRID 1528359
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HRID 1528359 반응식
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8](F)=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]([F:30])([F:29])[CH2:27][OH:28]>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8]([O:28][CH2:27][C:26]([F:30])([F:29])[F:25])=[CH:7][N:6]=1)=[O:4]
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참가 물질

5

반응물 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 66678591Methyl 4-(4-chlorophenyl)-5-fluoropyrimidine-2-carboxylate

생성물 1

HCID 666870874-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acid methyl ester수율 86.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

To a solution of 0.143 g 4-(4-chloro-phenyl)-5-fluoro-pyrimidine-2-carboxylic acid methyl ester in 1.5 ml dried DMSO was added 192 mg of cesium carbonate and 0.059 g of 2,2,2-trifluoroethanol and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was dried with MgSO4 and purified by chromatography on silica gel with a gradient of heptane:ethyl acetate=9:1 to 1:1 to yield 161 mg (86.60%) of the title compound as white solid, MS 347.1 (M+H)+.

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases were separated
  3. dry with materialthe organic phase was dried with MgSO4
  4. custompurified by chromatography on silica gel with a gradient of heptane

출처 및 근거

ORD 기록
ord-879c00dd4a8945709471aff1a9912f26
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090599B2

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