Triphenylphosphine → 4-tert-Butyl-N-{5-(2-benzothienyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)-ethoxy]pyrimidin-4-yl}benzenesulfonamide

HRID 1599023ノート

反応式

HRID 1599023 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.[S:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[CH:36]=[C:35]1[Sn](CCCC)(CCCC)CCCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C.[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.[Cu]Br.O1CCOCC1>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([S:21]([NH:20][C:3]2[C:2]([C:35]3[S:34][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[CH:36]=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

10

反応物 5

HCID 11776TriphenylphosphineHCID 522689Potassium FluorideHCID 2735461(1-Benzothiophen-2-yl)tributylstannaneHCID 11071742N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamideHCID 666371922,6-Di-t-butylcresol

生成物 1

HCID 98736364-tert-Butyl-N-{5-(2-benzothienyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)-ethoxy]pyrimidin-4-yl}benzenesulfonamide収率 83%

試薬・触媒・溶媒 4

HCID 24593copper(I) bromide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane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 (200 mg), 2-benzothienyl tributyltin (460 mg), bis(triphenylphosphine)palladium (II) chloride (51 mg), triphenylphosphine (28 mg), copper (I) bromide (21 mg), a few crystals of 2,6-di-tert-butylcresol and dioxane (6 ml) is refluxed for two hours. After cooling, the reaction solution is diluted with ethyl acetate and an aqueous potassium fluoride solution, and the mixture is stirred at room temperature for 60 minutes. The insoluble materials are removed by filtration, and the filtrate is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; methylene chloride:acetone=30:1), and recrystallized from ethyl acetate to give the title compound (182 mg).

後処理

  1. temperatureAfter cooling
  2. customThe insoluble materials are removed by filtration
  3. extractionthe filtrate is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; methylene chloride:acetone=30:1)
  9. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-22457c575d084090958bf23f41e06192
出典データセット
uspto-grants-1998_04
特許番号
US05739333

反応ノート

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