Triethylamine → N-cyclopentoxy-2-methyladenosine

Participants

Reaction Conditions

Reaction Steps

O-Cyclopentylhydroxylamine hydrochloride (0.52 g, 3.75 mmol) was reacted with 9-(2,3,5-triO-acetyl-β-D-ribofuranosyl)-6-chloro-2-methyl-9H-purine (1.07 g, 2.5 mmol) [prepared from 2-methylinosine (Journal of Organic Chemistry, 1967, 32, 3258-3260) by standard acylation and chlorination steps] in dioxan (40 ml) in the presence of triethylamine (0.63 g, 6.25 mmol). The reaction mixture was heated at 100° C. for 70 h, before being filtered and evaporated. The product (after purification by chromatography), followed by debenzoylation using methanolic ammonia to provide the title N-cyclopentoxy-2-methyladenosine (after column chromatography) as a foam 1H NMR (DMSO-d6)γ 1.47-1.93 (8H, m,--CH2CH2CH2CH2 --), 2.32 (3H, s,--CH3), 4.59 (1H, br m,--O--CH--), 5.88 (1H, d, H-1').

Provenance & Evidence