Triethylamine → HCID 22854323, compound

Participants

Reaction Steps

The above hydrochloride salt of 1-methyl-1-(2-phenylethyl)hydrazine (0.67 g, 1.05 mmol), 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.90 g, 3 mmol) and triethylamine (1.24 ml, 9 mmol) were dissolved in 1,4 -dioxan (20 ml). The solution was stirred at ambient temperature for 20 h. The cooled reaction mixture was evaporated to a gum and purified by flash chromatography on silica gel. Bution with cyclohexane/ethyl acetate (4/1) initially and then with a 1/1 mixture of these solvents provided 2',3',5'-tri-O-benzoyl-2-chloro-N-(N-methyl-N-(2-phenylethyl)amino)adenosine (1.28 g, 60%) as a foam, 1H NMR (DMSO-d6)γ 2.63 (3H, s,--CH3), 4.66 (1H, dd, H-5'a), 4.77 (1H, dd, H-5'b), 4.86 (1H, q, H-4'), 6.23 (1H, t, H-3'), 6.36 (1H, t, H-2'), 6.54 (1H, d, H-1'), 7.11-7.98 (20H, m, Ar-H), 8.44 (1H, s, H-8), 9.40 (1H, br s, N-H).

Provenance & Evidence