1,4-Dioxane → 4-tert-butyl-N-{5-(3,4-dimethoxyphenyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}benzenesulfonamide

HRID 1082266ノート

反応式

HRID 1082266 の反応式
Br[C:2]1[C:3]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([Sn](CCCC)(CCCC)CCCC)[CH:39]=[CH:40][C:41]=1[O:42][CH3:43].O1CCOCC1>C(OCC)(=O)C.[F-].[K+].[Cu]Cl>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([S:21]([NH:20][C:3]2[C:2]([C:39]3[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[C:41]([O:42][CH3:43])[CH:40]=3)=[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]3[N:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=3)[N:6]=[CH:5][N:4]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

参加物

7

反応物 3

HCID 312751,4-DioxaneHCID 10365179Tributyl(3,4-dimethoxyphenyl)stannaneHCID 11071742N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

生成物 1

HCID 117672524-tert-butyl-N-{5-(3,4-dimethoxyphenyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}benzenesulfonamide収率 74.3%

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒HCID 522689Potassium Fluoride溶媒

実験手順

A mixture of N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (100 mg), 3,4-dimethoxyphenyltributyltin (220 mg), bis(triphenylphsophine)palladium (II) chloride (26 mg), copper (I) chloride (11 mg), a few crystals of 2,6-di-tert-butylcrezol and dioxane (5 ml) is refluxed for 1.5 hour. After cooling, the reaction solution is diluted with ethyl acetate and aqueous potassium fluoride solution, and the mixture is stirred at room temperature for 30 minutes. The insoluble materials are removed by filtration, and the filtrate is acidified with 10% hydrochloric acid, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform/ethyl acetate=3:1), and recrystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{5-(3,4-dimethoxyphenyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}benzenesulfonamide (82 mg).

後処理

  1. temperatureAfter cooling
  2. customThe insoluble materials are removed by filtration
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is purified by preparative thin layer chromatography (solvent; chloroform/ethyl acetate=3:1)
  9. customrecrystallized from ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-235a6f20ce224342afb89c8ff0642213
出典データセット
uspto-grants-1996_12
特許番号
US05589478

反応ノート

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