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

HRID 9911

Reaction equation

HRID 9911 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-598185acff304cc3a86a995c03c157bb
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

Loading…