Ammonia → 2-chloro-N-[2-(phenylmethoxy)ethyl]adenosine

Participants

Reaction Steps

The title compound was prepared by reacting 2-(phenylmethoxy)ethylamine hydrochloride (0.51 g, 2.7 mmol) with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.43 g, 2.25 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro- N-[2-(phenylmethoxy)ethyl]adenosine (0.38 g, 44%)(after column chromatography) as a solid, mp 115°-124° C., 1H NMR (DMSO-d6)δ 3.50-3.58 (1H, m, H-5'a), 3.60-3.70 (4H, m, H-5'b, --CH2 -- and --CH--), 3.95 (1H, q, H-4'), 4.04-4.16 (2H, m, H-3' and --CH--), 4.52 (1H, br s, H-2' and --CH2 --), 5.07 (1H, t, 5'-0H), 5.21, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.22-7.36 (5H, m, Ar--H), 8.25-8.40 (2H, m, H-8 and N--H).

Provenance & Evidence