Water → 2-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine

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Reaction Steps

A suspension of potassium carbonate (4.1g) and 2-amino-6-chloropurine (5.0g) in dry dimethylformamide (120ml) was stirred for 20 minutes. 2-Benzoyloxyethoxymethyl-chloride (6.3g) was added and the resulting pink suspension stirred at room temperature for 6 days. The reaction mixture was then poured into a mixture of ice and water (210ml) with vigorous stirring. The aqueous mixture was extracted with chloroform (3 × 200ml), and the chloroform solution obtained was washed with a 5% acetic acid solution and then twice with water. The chloroform solution was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was redissolved in a minimal amount of chloroform and the resulting solution applied to a column containing silica gel (200g) in chloroform. The column was eluted with 2% methanol/98% chloroform and the eluant collected in 30ml cuts. The fractions containing 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (determined by TLC) were combined, evaporated and the residue recrystallized from benzene to give 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (2.0g., m.p. 130°-133.5° C.).

Provenance & Evidence