(+-)-2-Butanol → HCID 131717007, compound

Participants

Reaction Steps

A flask was charged with sodium hydride (60% oil dispersion, 300 mg, 7.5 mmol) which was washed with hexanes before the addition of (±)-cis-4-(2-amino-6-chloro-9H--purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (800 mg, 3 mmol) in ~10 mL of R-(-)-2-butanol. The solution was stirred at room temperature for 3 hours then at 60° C. (oil bath) for 1 hour. The solution was allowed to cool to room temperature before neutralization with 1 H HC1. The solution was concentrated and the residue chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform (0.81 g, 89%). Crystallization of such a sample from ethanol-acetonitrile yielded an off-white powder, m.p. 159-161° C.

Provenance & Evidence