Water → 4-(5-phenylpentylthio)-1-beta-D-ribofuranosyl-pyrazolo[3,4-d]pyrimidine

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Reaction Steps

Crude 5-phenylpentyl chloride (1.3 g) was added to a stirred solution of 4-mercapto-1-β-D-ribofuranosylpyrazolo [3,4-d]pyrimidine (2.0 g) and potassium bicarbonate (0.7 g) in N,N-dimethylformamide. The reaction mixture was heated on a steam bath for 25 hours. An additional 0.7 g of potassium bicarbonate was added and after heating for 1 hour more, the mixture was poured into water. The cooled aqueous mixture was extracted with chloroform. The chloroform soluble material was chromatographed on a silica gel column. The fractions containing the compound were combined and evaporated. Trituration with ether gave 0.4 g of crude product. This was dissolved in ethyl acetate and washed with water. The dried ethyl acetate solution was evaporated and purified by reversed phase chromatography in methanol water (80:20 vol/vol) to give 0.28 g of product m.p. 72°-75° C. (indefinite).

Provenance & Evidence