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

反応式

HRID 1082288 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d7e48ec3f564413cb89dfe8421734eda
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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