Reaction #10015

Reaction equation

2-chloro-6-(4-nitro-phenyl-amino)-purine

caesium carbonate

isopropyl iodide

dioxane

→

2-Chloro-9-isopropyl-6-(4-nitro-phenyl-amino)-9H-purine

Solvents

ethyl acetate

—

mixture

DMF

water

Conditions

Workup

1. 1
   Washthe organic phase is washed with water
2. 2
   Dryingdried over sodium sulfate
3. 3
   OtherAfter removal of the solvent
4. 4
   Otherthe residue is chromatographed over silica gel (mobile phase: CH2Cl2:methanol=9:1)
5. 5
   OtherThe crystalline precipitate obtained on concentration
6. 6
   Filtrationis filtered off
7. 7
   Otherdried

Procedure

A mixture comprising 0.87 g (3 mmol) of 2-chloro-6-(4-nitro-phenyl-amino)-purine, 0.15 g (4.5 mmol) of caesium carbonate and 1.8 ml (18 mmol) of isopropyl iodide is stirred in 22 ml of a mixture comprising dioxane:water:DMF in a ratio of 2:1:4 at 100° C. for 48 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: CH2Cl2:methanol=9:1). The crystalline precipitate obtained on concentration is filtered off and dried. 2-Chloro-9-isopropyl-6-(4-nitro-phenyl-amino)-9H-purine is obtained; m.p.>260° C.; FAB-MS: (M+H)+=333; Rf=0.8 (CH2Cl2:methanol=9:1).

Source