Hydrochloric Acid → 2-Methoxy-N-[(R)-1-phenoxy-2-propyl]adenosine

Participants

Reaction Steps

2-Methoxy- N-[(R)-1-phenoxy-2-propyl]adenosine was prepared by reacting 2-chloro- N-((R)1-phenoxy-2-propyl)adenosine (Example 2)(0.30 g, 0.69 mmol) with a mixture of sodium hydroxide (0.32 g, 8.0 mmol) and methanol (15 ml) in a sealed vessel at 80°-90° C. for 4 h. The cooled reaction mixture was neutralised with concentrated hydrochloric acid and evaporated to dryness. Water (30 ml) was added and the mixture was extracted with dichloromethane (2×30 ml). The combined extracts were dried (MgSO4) and coevaporated with dichloromethane (30 ml), giving the title compound as a foam (0.19 g, 60%), 1H NMR (DMSO-d6)δ 1.32 (3H, d, --CHC H3), 3.55 (1H, m, H-5'a), 3.65 (1H, m, H5'b), 3.72 (3H, s, --CH3), 3.91-3.99 and 4.10-4.20 (4H, 2 m, H-3', H-4' and --CH2 --), 4.51 (1H, dd, H-2'), 4.67 (1H, m, --C HCH3), 5.84 (1H, d, H-1'), 6.89-6.98 (3H, m, Ar--H), 7.26 (2H, dd, Ar--H) 8.12 (1H, br, --NH), 8.46 (1H, s, H-8).

Provenance & Evidence