Ammonia → HCID 10042350, compound

Participants

Reaction Steps

The title compound was prepared according to method A as described in example 4 by reacting O-methylhydroxylamine (0.20 g, 2.0 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.27 g, 2.0 mmol) and debenzoylating the purified product using methanolic ammonia to provide the title 2-chloro-N-methoxyadenosine (0.40 g, 45%) (after column chromatography) as a colourless foam which became crystalline on trituration with dichloromethane, providing 0.20 g of a white solid, mp 123°-125° C. 1H NMR (DMSO-d6)γ 3.52-3.59 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.78 (3H, s,--OCH3), 3.96 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.06 (1H, t, 5'-OH), 5.22, 5.51 (2H, 2d, 2'- and 3'-OH), 5.87 (1H, d, H-1'), 8.50 (1H, s, H-8), 11.60 (1H, s, N-H).

Provenance & Evidence