2-Chloroadenosine → HCID 15036649, compound

Participants

Reaction Steps

A mixture of 2-chloroadenosine (0.3 g) and 2-(tetrahydropyran-4-yl)ethylamine (1.15 g) is stirred under nitrogen at 140° for 6 hours. The mixture is concentrated to dryness at reduced pressure, the residue is dissolved in ethanol, the solution is treated with propylene oxide (2 ml) and stirred overnight. It is concentrated to dryness and chromatographed through a 25×180 mm column of silica gel, with methylene chloride and ammonia-saturated methanol (9:1) as eluent. The fractions containing the desired product are combined and concentrated at reduced pressure. The residue is dissolved in absolute ethanol and treated with ethanolic hydrogen chloride to form the hydrochloride salt of 2-[2-(tetrahydropyran-4-yl)ethyl-amino]adenosine; [alpha]D25 -13.6° (DMSO); m.p. 120°-130° dec.

Provenance & Evidence