2-Chloroadenosine → 2-((2-Cyclohexylethyl)amino)adenosine

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Reaction Steps

A mixture of 2-chloroadenosine (15.05 g) and 2-cyclohexylethylamine (31.75 g) is stirred under nitrogen at 140° over 6 hours. The reaction mixture is cooled to room temperature, diluted with ethanol (500 ml), propylene oxide (50 ml) is added and the mixture is stirred at room temperature for 3 hours. The solid is collected by vacuum filtration, washed with ethanol, then ether, and dried at 80°/0.1 mm over 16 hours. The white solid obtained is recrystallized from ethanol to yield 2-(2-cyclohexylethylamino)-adenosine, the compound of example 4q, m.p. 142°-145°, [alpha]D25 -30.5° (c=1, dimethyl sulfoxide).

Provenance & Evidence