Propylamine → [(1S,4R)-4-[2-amino-6-(propylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

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Reaction Steps

A solution of (±)-cis-4-(-2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.531 g, 2.00 mmol) from Example 4 and propylamine (1.12 g, 18.19 mmol) in 8 mL of ethanol was stirred at reflux for 2 hours. The solution was allowed to cool to room temperature before the addition of 2 mL of 1.0 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanolchloroform (0.46 g, 80%). Crystallization of such a sample from ethanol-ethyl acetate yielded a white powder, m.p. 138-140° C.

Provenance & Evidence