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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
ノート
印刷プレビュー

反応式

HRID 1528359 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-879c00dd4a8945709471aff1a9912f26
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090599B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート