Uridine → 5-(3-Aminopropyl)-2'-deoxyuridine

HRID 1975620Notes

Reaction equation

HRID 1975620 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1O.[C:18](#[N:21])[CH:19]=[CH2:20]>CO.[Pd]>[NH2:21][CH2:18][CH2:19][CH2:20][C:16]1[C:14](=[O:15])[NH:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:1]1[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:2]1

Participants

5

Reactant 2

HCID 6029UridineHCID 7855Acrylonitrile

Product 1

HCID 30811655-(3-Aminopropyl)-2'-deoxyuridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Uridine is reacted with mercuric chloride (5 mmol) at pH 5.0. The 5-mercurichloride-dU so produced is reacted with acrylonitrile and lithium tetrachloro-palladiate in methanol yielding 5-(2-cyanoethenyl) dU which is reduced by hydrogenation at 3 atmospheres in the presence of 10% palladium on charcoal in methanol.

Workup

  1. customThe 5-mercurichloride-dU so produced
  2. customyielding 5-(2-cyanoethenyl) dU which

Sources & evidence

ORD record
ord-f68c250589b3464d9b585b7a4ca7feae
Source dataset
uspto-grants-1994_02
Patent number
US05288609

Reaction notes

Loading…