Dichloromethane → HCID 22877230, compound

Participants

Reaction Steps

(R)-3-methyl-1-phenoxy-2-butylamine (0.6 g, 2.8 mmol) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.4 g, 2.2 mmol) in dioxan (20 ml) in the presence of triethylamine (0.5 g, 5.0 mmol). The reaction mixture was stirred at room temperature for 40 h before being filtered and evaporated. The product (after purification by flash chromatography) was debenzoylated with methanolic ammonia to provide the product (after column chromatography) as a foam which solidified on coevaporation with dichloromethane. 2-Chloro- N-[(R)-3-methyl-1-phenoxy2-butyl]adenosine (0.46 g, 44%) was obtained as a white solid, mp 95°-100° C., 1H NMR (DMSO-d6)δ 0.95, 0.98 (6H, 2d, 2×--CH3), 2.10 (1H, m, --C H(CH3)2), 3.53-3.60 (1H, m, H-5'a), 3.63-3.71 (1H, m, H-5'b), 3.95 (1H, q, H-4), 4.07-4.23 (3H, m, H-3' and --CH2 --), 4.96 (1H, m, --C--H), 4.56 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.23, 5.49 (2H, 2d, 2' and 3'-OH), 5.84 (1H, d, H-1'), 6.87-6.97 (3H, m, Ar--H), 7.24-7.31 (2H, dd, Ar--H), 8.36 (1H, d, --N--H), 8.40 (1H, s, H-8).

Provenance & Evidence