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

HRID 2271

反応式

HRID 2271 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-50229f9f65b24c3fbf8cc4093165ef6b
出典データセット
uspto-grants-1998_03
特許番号
US05728706

関連ノート

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