Potassium Carbonate → 7-(4-(4-Chlorobenzoyl)benzyl)-2,6-dichloropurine

HRID 1291204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291204
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>CN(C=O)C.O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29][N:6]3[C:5]4[C:9](=[N:10][C:2]([Cl:1])=[N:3][C:4]=4[Cl:11])[N:8]=[CH:7]3)=[CH:27][CH:26]=2)=[O:24])=[CH:33][CH:34]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 53244122,6-DichloropurineHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Produkt 1

HCID 189188407-(4-(4-Chlorobenzoyl)benzyl)-2,6-dichloropurineAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloropurine (3.25 g) in DMF (34 ml) was added potassium carbonate (2.85 g) as well as 4-(4-chlorobenzoyl)benzyl bromide (5.32 g) and the mixture was stirred at room temperature for 24 hours. This reaction mixture was diluted with water and extracted with ethyl acetate and the extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1-1:3) to provide the title compound (1.37 g, 19%) as colorless (anhydrous) powder. 1H-NMR (CDCl3) δ5.76(2H,s), 7.21-7.85(8H,m), 8.33(1H,s).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1-1:3)

Quellen und Nachweise

ORD-Eintrag
ord-d19090e6494d44c59a17ba9d9a09e0c0
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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