Ammonia → HCID 86748757, compound

Participants

Reaction Steps

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2-methylthio-9H-purine (0.50 g, 1.1 mmol) (prepared by Method C, using the procedure described in PCT Publication No. WO 93/08206, O-[2-(phenoxy)ethoxy]hydroxylamine hydrochloride (0.41 g, 2.16 mmol) (see Example 9) and triethylamine (0.45 g, 4.4 mmol) were stirred at 100° C. in dioxan (20 ml) for 6 h, and at ca. 95° C. for 65 h. The product, after column chromatography, was deprotected using methanolic ammonia, to provide the title 2-methylthio-N-[2-(phenoxyethoxy]adenosine (0.09 g, 18%), (after column chromatography) as a colourless foam, tic Rf 0.26 [(SiO2, dichloromethane/methanol (9/1)], 1H NMR (DMSO-d6)γ 2.51 (3H, s,--SCH3), 3.52-3.60 (1H, m, H-5'a), 3.62-3.69 (1H, m, H-5'b), 3.94 (1H, q, H- 4'), 4.16 (1H, q, H-3'), 4.30 (4H, br d,--OCH2CH2O--), 4.61 (1H, q, H-2'), 5.04 (1H, t, 5'-OH), 5.23, 5.50 (2H, 9d, 9'- and 3'-OH), 5.90 (1H, d, H-1'), 6.92-7.01 (3H, m, Ar-H), 7.32 (2H, dd, Ar-H), 8.36 (1H, s, H-8), 11.20 (1H, s, N-H).

Provenance & Evidence