Toluene → 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

HRID 1082265

反応式

HRID 1082265 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH2:18])[C:13]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=N[CH:7]=1.[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27].[OH-].[K+].[C:43]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:18][C:14]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[CH:43]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=3)[N:17]=[CH:16][N:15]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27]

参加物

7

反応物 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 117291026-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amineHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

生成物 1

HCID 196894884-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 25517Ammonium Chloride溶媒

実験手順

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1)
  7. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-b065fb797d834479958f8737ac1e6783
出典データセット
uspto-grants-1996_12
特許番号
US05589478

関連ノート

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