Triethylamine → HCID 22877229, compound

Participants

Reaction Steps

(R)-2-Phenoxy-1-propylamine (0.6 g, 2.9 mmol)(prepared by the method described in example 2) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.5 g, 2.4 mmol) in dioxan (20 ml) in the presence of triethylamine (0.5 g, 5.3 mmol). The reaction mixture was stirred at room temperature for 72 h before being filtered and evaporated. The product, following purification by flash chromatography, was treated with saturated methanolic ammonia (30 ml) for 18 h and evaporated to provide a solid residue. This solid was washed thoroughly with dichloromethane to provide the title 2-chloro- N-[(R)-2-phenoxy-1-propyl]adenosine (0.7 g, 65%), mp 175°-177° C., 1H NMR (DMSO-d6)δ 1.39 (3H, d, --CH3), 3.56 (1H, ABX, H-5'a), 3.68 (1H, m, H-5'b), 3.33-3.40 (1H, m, --C--H), 3.83-3.92 (1H, --C--H), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.53 (1H, dd, H-2'), 4.70 (1H, q, --C--H), 5.08, 5.34, 5.50 (3H, 3 br, 2', 3' and 5'-OH), 5.85 (1H, d, H-1'), 6.90 (1H, t, Ar--H), 7.11 (2H, d, Ar--H), 7.28 (2H, t, Ar--H), 8.45 (1H, s, H-8), 8.63 (1H, t, N--H).

Provenance & Evidence