Lithium azide → Uridine, 5'-azido-2',5'-dideoxy-

HRID 1974221Notes

Reaction equation

S(O[CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:15][C@@H:14]1[OH:26])(C1C=CC(C)=CC=1)(=O)=O.[N-:27]=[N+:28]=[N-:29].[Li+]>CN(C)C=O>[N:27]([CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:15][C@@H:14]1[OH:26])=[N+:28]=[N-:29]

Participants

Conditions

Temperature: 100 °C

Procedure

5' -O-Tosyl-2'-deoxyuridine (2.78 gm, 10 mmole) is dissolved in 50 ml of dimethylformamide (DMF) and 0.98 gm (20 mmole) of lithium azide added. The solution is heated at 100° C for 2 hours, then cooled and filtered. DMF is removed in vacuo at 40° and the yellow residue dissolved in 200 ml of 50% aqueous methanol. 20 gm of Dowex 50 (H+) resin are added and the solution stirred at room temperature for 30 minutes. After filtration, the solvent is reduced to 20-30 ml by rotary evaporation. As the solution becomes more and more concentrated, a white precipitate forms. The precipitate is collected by filtration, dried in vacuo over KOH pellets and recrystallized from 2-propanol to yield 2.05 gm (80% yield) of a white powder.

Workup

temperaturecooled
filtrationfiltered
customDMF is removed in vacuo at 40°
dissolutionthe yellow residue dissolved in 200 ml of 50% aqueous methanol
addition20 gm of Dowex 50 (H+) resin are added
filtrationAfter filtration
customthe solvent is reduced to 20-30 ml by rotary evaporation
concentrationmore concentrated
filtrationThe precipitate is collected by filtration
dry with materialdried in vacuo over KOH pellets
customrecrystallized from 2-propanol

Sources & evidence

ORD record: ord-40fa898f3a77422183af54fe65bff401
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04000260

Reaction notes

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