Cytidine, 3'-azido-2',3'-dideoxy- → 84472-90-2

HRID 364007Notes

Reaction equation

HRID 364007 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[CH:17][C:15]([NH2:16])=[N:14][C:12]2=[O:13])[CH2:5]1)=[N+]=[N-].[H][H]>[Pd]>[NH2:1][C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[CH:17][C:15]([NH2:16])=[N:14][C:12]2=[O:13])[CH2:5]1

Participants

4

Reactant 2

HCID 451374Cytidine, 3'-azido-2',3'-dideoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 7351584472-90-2

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

An alternate synthesis of compound (XIII) involves treatment of 3,-azido-5'-0-acetyl-2',3'-dideoxyuridine (X) with 4-chlorophenylphosphorodichloridate and 1,2,4-triazole in pyridine at room temperature for 3 days to give the 4-trizolylpyrimidinone derivative. Subsequent treatment with aqueous ammonia in dioxane (1:3 v/v) for 4 hours, then saturated methanolic ammonia overnight at room temperature, yields the 3'-azido analog (XII). Compound (XII) is then reduced under 50 psi of hydrogen in the presence of 10% palladium on charcoal at room temperature for 6 hours to obtain the desired 3'amino-2',3'-dideoxycytidine derivative (XIII).

Sources & evidence

ORD record
ord-fc232f426c2b4f81bf3efef1180280fc
Source dataset
uspto-grants-1986_08
Patent number
US04604382

Reaction notes

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