Thymidine, 5'-azido-5'-deoxy- → 5'-Amino-5'-deoxythymidine

HRID 2117802Notes

Reaction equation

HRID 2117802 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19])=[N+]=[N-]>CO.[H][H]>[NH2:1][CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19]

Participants

4

Reactant 1

HCID 451456Thymidine, 5'-azido-5'-deoxy-

Product 1

HCID 653115'-Amino-5'-deoxythymidine

Reagents, catalysts & solvents 2

HCID 178418361HCID 178418361, compoundCatalystHCID 887MethanolSolvent

Procedure

The thus-obtained 5′-azido-5′-deoxythymidine was then dissolved in methanol and reduced with hydrogen using 10% palladium/carbon as a catalyst, whereby 5′-amino-5′-deoxythymidine was obtained. Yield 1.734 g, 71.6%.

Sources & evidence

ORD record
ord-0b0026db5ac14b5e9d7b39fad658d0cf
Source dataset
uspto-grants-2008_10
Patent number
US07442788B2

Reaction notes

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