Potassium Carbonate → HCID 14236876, compound

Participants

Reaction Steps

A solution of 3.36 g (6.8 mmoles) of 1,1-bis(benzoyloxymethyl)-2-p-toluenesulfonyloxymethylcyclopropane in 15 ml of dry DMF (dimethylformamide) was added to a mixture of 1.37 g (8.2 mmoles) of 2-amino-6-chloropurine and 1.2 g (8.8 mmoles) of K2CO3 in 20 ml of DMF. The mixture was heated to 60° and stirred for 4 hours. The reaction was monitored by TLC in chloroform-methanol-water (95:5:0.3) Rf 0.15, 0.9 (starting material), 0.4, 0.6 (Product). The reaction mixture was concentrated and the residue dissolved in 60 ml of CHCl3 --MeOH (1:1). About 20 ml of silica gel was added and the mixture was concentrated to dryness. The residue was added to the top of a 200 ml silica gel column and chromatographed in CMW (chloroform-methanol-water) (97.5:2.5:0.15). Fractions containing the two products (the 9 and 7 isomers) were cooled separately and concentrated to give 1.79 g (53%) of the title compound and 170 mg (5.1%) of the 7-isomer.

Provenance & Evidence