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Water → 4-((4-Chloro-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrile

HRID 2284765
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Reaktionsgleichung

Reaktionsgleichung von HRID 2284765
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[CH2:18]([N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])[CH2:19][CH2:20][C:21]#[CH:22].C(OCC)(=O)C.O>CN(C)C=O.C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:22]#[C:21][CH2:20][CH2:19][CH2:18][N:23]2[C:24](=[O:33])[C:25]3[C:26](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:28])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1
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Komponenten

9

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11769822N-(4-Pentynyl)phthalimideHCID 900517824-((4-Chloro-5-iodopyrimidin-2-yl)amino)benzonitrile

Produkt 1

HCID 900521494-((4-Chloro-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrileAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 4-((4-chloro-5-iodopyrimidin-2-yl)amino)benzonitrile (J12, 53 mg) and N-(4-pentynyl)phthalimide (47 mg) in N,N-dimethylformamide (1 mL), triethylamine (103 μL), copper(I) iodide (14 mg), and bis(triphenylphosphine)palladium(II) dichloride (10 mg) were added at room temperature, and the mixture was stirred overnight at the same temperature. To the reaction mixture, ethyl acetate and water were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid matter was washed with chloroform, and then dried under reduced pressure to obtain 4-((4-chloro-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrile (J13, 44 mg) as white solid.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe obtained solid matter was washed with chloroform
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f6db0eab4f844b88722105a33c7f238
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145415B2

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