Dimethylformamide → 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine

HRID 9911

Reaktionsgleichung

Reaktionsgleichung von HRID 9911
[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][CH:15]=[C:14]([F:18])[CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:26][CH3:27].CN(C=O)C>O1CCOCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:26][CH3:27])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 219883282-Chloro-6-(3-fluoro-phenyl-amino)-purine

Produkt 1

HCID 219883192-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

1 g (3.47 mmol) of 2-chloro-6-(3-fluoro-phenyl-amino)-purine, 1.8 g (5.5 mmol) of caesium carbonate and 2.3 ml (27.8 mmol) of iodoethane are stirred in 14 ml of a dioxane/water mixture (4:3) and 12 ml of DMF at RT for 16 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phase is washed with water and dried over sodium sulfate. After removal of the solvent, the residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane=4:1) and 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine is isolated; m.p. 136° C.; FAB-MS: (M+H)+=292; Rf=0.7 (CH2Cl2:methanol=9:1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-598185acff304cc3a86a995c03c157bb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091346B1

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