1,4-Dioxane → 4-tert-butyl-N-[6-{2-(5-(2-thienyl)pyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide

HRID 1082288

반응식

HRID 1082288 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35](Br)=[CH:34][N:33]=3)[N:18]=[C:17]([CH2:39][CH2:40][CH3:41])[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[Sn](CCCC)(CCCC)CCCC.O1CCOCC1.[F-].[K+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([C:43]4[S:42][CH:46]=[CH:45][CH:44]=4)=[CH:34][N:33]=3)[N:18]=[C:17]([CH2:39][CH2:40][CH3:41])[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 522689Potassium FluorideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 19689505N-{6-[2-(5-Bromo-pyrimidin-2-yloxy)-ethoxy]-2-propyl-5-p-tolyl-pyrimidin-4-yl}-4-tert-butyl-benzenesulfonamide

생성물 1

HCID 196895274-tert-butyl-N-[6-{2-(5-(2-thienyl)pyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide수율 69.3%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-tert-butyl-N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (300 mg), 2-thienyltributyltin (670 mg), bis(triphenylphosphine)palladium (II) chloride (16 mg) and dioxane (5 ml) is refluxed for 80 minutes. After cooling, the reaction solution is diluted with ethyl acetate, and thereto is added 10% aqueous potassium fluoride solution. The mixture is stirred at room temperature for one hour, and the reaction solution is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=30:1~10:1), and crystallized from methylene chloride/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(2-thienyl)pyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (209 mg) as crystals.

후처리

  1. temperatureis refluxed for 80 minutes
  2. temperatureAfter cooling
  3. washthe reaction solution is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=30:1~10:1)
  8. customcrystallized from methylene chloride/n-hexane

출처 및 근거

ORD 기록
ord-d7e48ec3f564413cb89dfe8421734eda
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05589478

연결된 노트

불러오는 중…