1-Phenoxy-2-propanamine → HCID 22877232, compound

Participants

Reaction Steps

1-Phenoxy-2-propylamine (0.33 g, 2.18 mmol) was reacted with 6-chloropurine riboside (i.e. 9-β-D-ribofuranosyl-9H-purine)(0.5 g, 1.7 mmol) in dioxan (30 ml) in the presence of diisopropylethylamine (0.28 g, 2.2 mmol). The reaction mixture was heated at reflux for 5 h, cooled and evaporated. The residue was purified by flash chromatography on silica gel to provide the N-(1-Phenoxy-2-propyl)adenosine (a mixture of diastereoisomers) as a foam (0.06 g, 7%), 1H NMR (DMSO-d6)δ 1.32 (3H, d, --CH3), 3.52-3.60 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.93-3.99 and 4.12-4.20 (4H, 2m, m, H-4', H-3' and --CH2 --), 4.62 (1H, q, H-2'), 4.68-4.82 (1H, m, --C HCH3), 5.40 (1H, t, 5'-0H), 5.20, 5.45 (2H, 2d, 2'- and 3'-OH), 5.90 (1H, d, H-1'), 6.88-6.98 (3H, m, Ar--H), 7.23-7.31 (2H, t, Ar--H), 7.85, 8.21, 8.38 (3H, 3s, H-2, H-8 and N--H).

Provenance & Evidence