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

HRID 1599023노트

반응식

HRID 1599023 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.[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]

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 24593copper(I) bromide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-22457c575d084090958bf23f41e06192
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739333

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