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

HRID 618962Notes

Reaction equation

[N:1]([C@@H:4]1[C@H:8]([OH:9])[C@@H:7]([CH2:10][OH:11])[O:6][C@H:5]1[N:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14])=[N+:2]=[N-:3].[I:20]Cl.CCOCC>CO>[I:20][C:18]1[C:16](=[O:17])[NH:15][C:13](=[O:14])[N:12]([CH:19]=1)[C@@H:5]1[O:6][C@H:7]([CH2:10][OH:11])[C@@H:8]([OH:9])[C@H:4]1[N:1]=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

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, JH2',H3' =5.3 Hz), 4.01 (m, 1H, H4'), 3.91 (dd, 1H, H5'AJgem =12.3 Hz, JH5',H4' =2.4 Hz) 3.76 (dd, 1H, H5'B, 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.

Workup

temperatureAfter cooling to room temperature
filtrationthe white precipitate is filtered off
customevaporated to dryness

Sources & evidence

ORD record: ord-ee7540994944416a992db233533e6cd1
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958691

Reaction notes

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