Citric Acid → HCID 9932711, compound

Participants

Reaction Steps

The title compound was prepared by reacting 1-phenoxy-2-propylamine (16.62 g, 0.11 mol) with 9-(2,3,5-tri- O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (24.6 g, 55 mmol) in dioxan (250 ml) in the presence of triethylamine (7.23 g, 71.5 mmol) followed by deprotection of the product using a solution of sodium (0.15 g, 6.5 mmol) in methanol (250 ml). The reaction mixture was neutralized with citric acid, and treated with a mixture of ethyl acetate (300 ml) and water (200 ml). The ethyl acetate phase was separated, dried (MgSO4) and evaporated before being purified by flash chromatography on silica gel, eluting initially with dichloromethane, and later with a mixture of dichloromethane and ethanol (9:1). This provided the title 2-chloro- N-(1-phenoxy-2-propyl)adenosine (18.2 g, 76%)(a mixture of diastereoisomers) as an amorphous foam, 1H NMR (DMSO-d6)δ 1.31 (3H, d, --CH3), 3.53-3.59 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.06-4.20 (3H, 2 m, H-3' and --CH2 --), 4.54 (1H, m, H-2'), 4.65 (1H, m, --C HCH3), 5.07 (1H, t, 5'-0H), 5.21, 5.50 (2H, 2d, 2'- and 3'--OH), 5.84 (1H, d, H-1'), 6.87-7.00 (3H, m, Ar--H), 7.23-7.32 (2H, t, Ar--H), 8.31-8.45 (2H, m, H-8 and N--H).

Provenance & Evidence