6-(Phenylmethoxy)-9H-purin-2-amine → HCID 14154536, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.41 g (10 mmole) of 2-amino-6-benzyloxypurine [M. J. Robins and R. K. Robins, J. Org. Chem., 24, 2160 (1969)] in 24 ml of dry DMF was treated with 0.44 g (11 mmole) of sodium hydride (60% dispersion in oil). The mixture was stirred under nitrogen as hydrogen was evolved. After gas evolution had ceased and a clear solution had formed, a solution of 3.46 g (11 mmole) of (±)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propyl p-toluene-sulfonate (prepared as above) in 2 ml of DMF was added. The mixture was stirred at 60° C. for 3 days. The cooled mixture was then neutralized with glacial acetic acid and concentrated in vacuo. The residue was taken up in ethyl acetate, filtered, re-concentrated and chromatographed on silica gel (elution with ethyl acetate). Evaporation of fractions containing clean product gave a residue which, on trituration with ether, yielded 975 mg (25%) of white crystals, mp 111°-112° C. The analytical batch, similarly prepared, had m.p. 115.5°-118°.

Provenance & Evidence