Lithium azide → 2,2'-Anhydrouridine

HRID 634884Notes

Reaction equation

HRID 634884 reaction equation
N([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+]=[N-].[N-]=[N+]=[N-].[Li+]>CN(P(N(C)C)(N(C)C)=O)C>[CH:18]1[C:16](=[O:17])[N:15]=[C:13]2[N:12]([C@@H:5]3[O:6][C@H:7]([CH2:10][OH:11])[C@@H:8]([OH:9])[C@@H:4]3[O:14]2)[CH:19]=1

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 16862926929-65-7

Product 1

HCID 8061382,2'-AnhydrouridineYield 50%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

The synthesis of 2′-azido-2′-deoxyuridine (ADU) has been previously published (Moffat et al. (1971) J. Org. Chem. 36:250). According to this procedure, anhydrouridine is treated with 7.1 equivalents of lithium azide in HMPA at 150° C. The desired product is obtained in only 50% yield after separation from a number of by-products. It is desirable to have a process by which ADU is synthesized in high yield without the necessity of further purification by chromatographic processes. Furthermore, it is desirable to avoid the use of HMPA, a known carcinogen.

Sources & evidence

ORD record
ord-26207023ed754fd19ec1bb989dd06bb6
Source dataset
uspto-grants-2001_02
Patent number
US06184364B2

Reaction notes

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