Diethyl Ether → 2'-Azido-2'-deoxy-5-iodouridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2′-azido,2′-deoxyuridine (2.5 g, 9.3 mmoles) in methanol (20 ml) is added ICl (3.3 g, 20.5 mmoles, 2.2 eq.). The mixture is heated at 50° C. for 30 min. After cooling to room temperature, an equal volume of ether is added and the white precipitate is filtered off. The precipitate is stirred in methanolic ammonia (20 ml) at room temperature for 15 min, and then evaporated to dryness to yield 2.81 g (76%) of 5-iodo,2′-azido,2′-deoxyuridine. 1H NMR (300 MHz, methanol -d4) δ 8.58 (s, 1H, H6), 5.88 (d, 1H, H1′, JH1′,H2′=3.5 Hz), 4.46 (t, 1H, H3′, J=5.8 Hz), 4.11 (dd, 1H, H2′, JH1′,H2′=3.9 Hz, J H2′,H3′=5.3 Hz), 4.01 (m, 1H, H4′), 3.91 (dd, 1H, H5′λJgem=12.3 Hz, JH5′,H4′=2.4 Hz) 3.76 (dd, 1H, H5′β, Jgem=12.3 Hz, JH5′,H4′=2.4 Hz). 13C NMR (75 MHz, methanol-d4) δ 163.03, 152.17, 146.50, 88.88, 86.18, 71.21, 67/67, 61.00, 48.15. FAB mass spectrum, (M+H) m/z 396.

Provenance & Evidence