Floxuridine → 2'-deoxy-5-fluoro-3'-O-(1-naphthylmethyl)-uridine

HRID 466097Notes

Reaction equation

HRID 466097 reaction equation
[OH-].[K+].[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1.[C:20]1([CH2:30]Br)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>>[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([O:12][CH2:30][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 5790FloxuridineHCID 14797Potassium HydroxideHCID 1378441-(Bromomethyl)naphthalene

Product 1

HCID 140744062'-deoxy-5-fluoro-3'-O-(1-naphthylmethyl)-uridineYield 18%

Procedure

The general procedures of Reference Examples 4 and 5 were followed using 1.3 g of potassium hydroxide, 1.00 g of 2'-deoxy-5-fluorouridine and 2.7 g of 1-naphthylmethyl bromide, thereby producing 0.28 g of the title compound in a yield of 18%.

Sources & evidence

ORD record
ord-d6c8084ee8ec40b2a2eb6cbd64127813
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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