Ammonia → HCID 53887934, compound

Participants

Reaction Steps

The title compound was prepared according to method A by reacting 1-methyl-1-(2-phenoxyethyl)hydrazine (prepared by the general method described in example 1) (0.80 g, 4 mmol) and 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.53 g, 4 mmol) and triethylamine (1.11 ml, 8 mmol) in dioxan (25 ml), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro-N-(N-methyl-N-(2-phenoxyethyl)amino)adenosine (0.84 g, 47%) (after column chromatography) obtained as a solid, mp 166°-8° C., 1H NMR (DMSO-d6)γ 2.70 (3H, s, --CH3), 3.22 (2H, br t, --CH2 --), 3.51-3.58 (1H, m, H-5'a), 3.62-3.69 (1H, m, H-5'a), 3.95 (1H, q, H-4'), 4.05-4.15 (3H, m, --CH2 -- and H-3' ), 4.50 (1H, q, H-2'), 5.06 (1H, t, 5'-OH), 5.21, 5.49 (2H, 2d, 2'- and 3--OH), 5.81 (1H, H-1'), 6.79-7.25 (5H, m, Ar-H), 8.41 (1H, s, H-8), 9.41 (1H, br s, N-H).

Provenance & Evidence