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

HRID 1082266노트

반응식

HRID 1082266 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 8857Ethyl Acetate용매HCID 522689Potassium Fluoride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-235a6f20ce224342afb89c8ff0642213
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05589478

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