Sodium Azide → Uridine, 5'-azido-2',5'-dideoxy-

HRID 1818660Notes

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].[Na+]>CN(C=O)C>[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: 95 °C

Procedure

To a solution of 5′-O-tosyl-2′-deoxyuridine (13.591, 0.035 mol) in dry DMF (90 mL) was added NaN3 (9.29 g, 0.141 mol) and the reaction mixture was allowed to stir at 95° C. for 12 h. The reaction mixture was cooled, the solid residue was removed by filtration and the filtrate was concentrated under vacuum to give the crude product. The crude was purified by column chromatography on silica gel (4% methanol in chloroform) which gave the title product (5.29 g, 56%) as a white solid.

Workup

temperatureThe reaction mixture was cooled
customthe solid residue was removed by filtration
concentrationthe filtrate was concentrated under vacuum
customto give the crude product
customThe crude was purified by column chromatography on silica gel (4% methanol in chloroform) which

Sources & evidence

ORD record: ord-df49a9b2e00949efb3710c97ccfeca95
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601702B2

Reaction notes

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