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

HRID 9917

Reaction equation

HRID 9917 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][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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aafe9cd2ac154742ae3af14c87c79dc2
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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