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

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Reaction Steps

(±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.400 g, 1.5 mmol) from Example 4 and dimethylamine (25% aqueous solution, 20 mL) was stirred at 80° C. for 0.5 hours. The reaction mixture was allowed to cool to room temperature before the addition of 1.5 mL of 1 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanol-chloroform (0.310 g, 75%). Crystallization of such a sample from ethanol-water gave an off-white powder m.p. 173-174° C.:

Provenance & Evidence