Ammonia → 2-Chloro-N-(2-phenoxyethyl)adenosine

Participants

Reaction Steps

The title compound was prepared by reacting 2-phenoxyethylamine hydrochloride (0.80 g, 4.6 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol) in dioxan (25 ml) in the presence of triethylamine (1.0 g, 9.6 mmol) followed by deprotection of the purified product using methanolic ammonia to provide the title nucleoside (0.75 g, 60%)(following flash chromatography) as an amorphous foam, 1H NMR (DMSO-d6)δ 3.52-3.59 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.82 (2H, q, --OH2 --), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.52 (1H, q, H-2'), 5.12 (1H, t, 5'-0H), 5.25, 5.54 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 6.92-7.02 (3H, m, Ar--H), 7.26-7.34 (2H, t, Ar--H), 8.46 (1H, m, H-8), 8.56 (1H, br, t, N--H).

Provenance & Evidence