Triethylamine → HCID 22877225, compound

Participants

Reaction Steps

(R)-1-(4-fluorophenoxy)-2-propylamine (0.29 g, 1.4 mmol)(prepared from 4-fluorophenol by the method desrcribed in example 2) was reacted with 9-(2',3',5'-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.89 g, 1.4 mmol) in dioxan (30 ml) in the presence of triethylamine (0.42 g, 3 mmol). The reaction mixture was stirred at room temperature for 18 h, and heated at 60° C. for 4 h. The reaction mixture was filtered and evaporated to a residue which was purified by flash chromatography. The resultant 2',3',5'-tri- O-benzoyl-2-chloro- N-[(R)-1-(4-fluorophenoxy)-2-propyl]adenosine was deprotected using methanolic ammonia to provide the title 2-chloro- N-[(R)-1-(4-fluorophenoxy)-2-propyl]adenosine (0.21 g, 40%)(after column chromatography), mp 172°-173° C.; 1H NMR (DMSO-d6)δ 1.29 (3H, d, --CH3), 3.52-3.60 (1H, m, H-5'a), 3.64-3.72 (1H, m, H-5'b), 3.92-4.00 (2H, m, H-4' and --C--H), 4.05-4.20 (2H, m, H-3' and --C--H), 4.53 (1H, m, H-2'), 4.65 (1H, m, --CH3C H--), 5.08, 5.24, 5.50 (3H, 3 br, 2', 3' and 5'-OH), 5.86 (1H, d, H-1'), 6.89-7.15 (4H, 2 m, Ar--H), 8.30-8.46 (2H, m, H-8 and N--H).

Provenance & Evidence