Adenine → 2-Methyladenine

Participants

Reaction Steps

To a suspension of 114 mg (2.85 mmol) of 60% sodium hydride (previously washed with hexane) in 18 ml of anhydrous dimethylformamide 386 mg (2.85 mmol) of adenine was added, and the mixture was stirred for 20 minutes at room temperature. Then, 1.18 g (2.38 mmol) of (Z)-[1,2-bis(benzoyloxymethyl)] cyclopropylmethyl p-toluenesulfonate obtained in Example 1 in 6 ml of anhydrous dimethylformamide was added and the mixture was stirred for 3 hours at 60° C. The solvent was distilled off, and dichloromethane and a saturated aqueous solution of sodium bicarbonate was added to the residue. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The resulting residue was subjected to silica gel chromatography (4-10% methanol/dichloromethane) to get 844 mg (1.84 mmol, 77%) of (±)9-[1'α, 2'β-bis-(benzoyloxy methyl) cyclopropan-1'β-yl] methyladenine and 52.8 mg (0.115 mmol), 5 %) of (±)7-[1'α2'β-bis-(benzoyloxymethyl) cyclopropan-1'β-yl] methyladenine.

Provenance & Evidence