Isopropyl iodide → 2-chloro-9-isopropyl-6-(4-fluoro-phenyl-amino)-9H-purine

HRID 9917

Reaktionsgleichung

Reaktionsgleichung von HRID 9917
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:25](I)([CH3:27])[CH3:26].O1CCOCC1>C(OCC)(=O)C.CN(C=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:25]([CH3:27])[CH3:26])=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[N:3]=1

Komponenten

8

Edukt 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 219881932-Chloro-6-(4-fluoro-phenyl-amino)-purine

Produkt 1

HCID 219882462-chloro-9-isopropyl-6-(4-fluoro-phenyl-amino)-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture comprising 1 g (3.3 mmol) of 2-chloro-6-(4-fluoro-phenyl-amino)-purine, 2.1 g (6.6 mmol) of caesium carbonate and 2 ml of isopropyl iodide is stirred in 32 ml of a mixture comprising dioxane, water and DMF in a ratio of 2:3:7 at 100° C. for 20 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phase is washed with water. After drying over sodium sulfate and removal of the solvent, the residue is chromatographed over silica gel (mobile phase: ethyl acetate:hexane=4:1). On concentration, 2-chloro-9-isopropyl-6-(4-fluoro-phenyl-amino)-9H-purine is obtained as a crystalline compound. m.p. 154° C.; FAB-MS: (M+H)+=306; Rf=0.2 (ethyl acetate:hexane=4:1).

Aufarbeitung

  1. washthe organic phase is washed with water
  2. dry with materialAfter drying over sodium sulfate and removal of the solvent
  3. customthe residue is chromatographed over silica gel (mobile phase: ethyl acetate:hexane=4:1)
  4. concentrationOn concentration

Quellen und Nachweise

ORD-Eintrag
ord-aafe9cd2ac154742ae3af14c87c79dc2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091346B1

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