Cesium carbonate → 2-(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol

HRID 2067899ノート

反応式

HRID 2067899 の反応式
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][OH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:24][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=3)[O:23][CH2:26][CH2:27][OH:28])=[N:12][CH:11]=2)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 687295593-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenol

生成物 1

HCID 687282992-(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenol 39 (1.2 mmol), 2-bromoethanol (1.4 mmol) and cesium carbonate (1.6 mmol) in acetonitrile (10 mL) is heated to 85° C. for 12 h then cooled to rt. The reaction is evaporated to dryness then re-dissolved in DCM. The organic mixture is washed with water and brine then dried over magnesium sulfate, filtered and reduced to dryness. Purification by silica gel chromatography with hexane:EtOAc=1:1 as eluant affords 2-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethanol 40a as white solid. MS (m/z) (M+1)+: 373.8.

後処理

  1. customThe reaction is evaporated to dryness
  2. dissolutionthen re-dissolved in DCM
  3. washThe organic mixture is washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customPurification by silica gel chromatography with hexane

出典と根拠

ORDレコード
ord-77cc3b521a5e4bbdb994ecb109001f92
出典データセット
uspto-grants-2012_10
特許番号
US08293757B2

反応ノート

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