Adenine → HCID 14236877, compound

Participants

Reaction Steps

A suspension of 965 mg (7.14 mmoles) of adenine in 25 ml of dry DMF was stirred and 171 mg (7.14 mmoles; 286 mg of 60%) NaH emulsion was added. All of the NaH had reacted after 30 minutes and a solution of 3 g (6.5 mmoles) of 1,1-bis(benzoyloxymethyl)-2-(p-toluenesulfonyloxymethyl)cyclopropane (Example 2, product of Step D) in 10 ml of DMF was added and the mixture was heated at 40°. TLC in CMW (90:10:1), Rf 0.2, 0.95 (starting materials) 0.45, 0.55 (products) showed that the reaction was complete in 3 hours. The mixture was concentrated to dryness and the residue was triturated with three 20 ml portions of ether, filtered and dried. The resultant solid was washed with twenty 3 ml portions of water and dried (1.2 g, largely a mixture of the two isomeric products). One gram of the crude product was chromatographed on five 2000 micron silica gel plates in CMW (95:3:0.3) and the zones (UV absorbing) at Rf 0.29 and 0.18 (the 9 and 7 isomers, respectively) were eluted with CMW (70:30:3). After concentration of the solvents, there was obtained 670 mg (25%) of the title compound and 78 mg (2.5%) of the 7-isomer.

Provenance & Evidence