Iodoethane → 2-chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine

HRID 9902

Reaktionsgleichung

Reaktionsgleichung von HRID 9902
[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]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28](I)[CH3:29]>O1CCOCC1.O.CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:28][CH3:29])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:3]=1

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 219882372-Chloro-6-(3-trifluoromethyl-phenyl-amino)-purine

Produkt 1

HCID 219881872-chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 86622776DMF dioxane waterLösungsmittel

Versuchsvorschrift

A mixture comprising 1 g (3.2 mmol) of 2-chloro-6-(3-trifluoromethyl-phenyl-amino)-purine, 1.7 g (5.1 mmol) of caesium carbonate and 2.1 ml (25.6 mmol) of ethyl iodide in 7 ml of dioxane/water/DMF (8:2:2) is stirred at RT for 18 h. It is then diluted with ethyl acetate and the organic phase is washed with water. This phase is separated off and dried over sodium sulfate. After removal of the solvent, the residue is recrystallized from ethyl acetate and diethyl ether. 2-Chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine is obtained; m.p. 129–130° C.; FAB-MS: (M+H)+=342; Rf=0.6 (methylene chloride:methanol=9:1).

Aufarbeitung

  1. washthe organic phase is washed with water
  2. customThis phase is separated off
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue is recrystallized from ethyl acetate and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-bf83831a158f40d799e226584860bcea
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091346B1

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