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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 13
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Original Articles

On the Alkylation of 5-Fluorouracil-Some Recent Findings

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Pages 1047-1054 | Published online: 06 Dec 2006
 

Abstract

Since its discovery 5-fluorouracil 1(1,5-FU), an important anticancer drug, has been the subject of study for the preparation of some suitable derivatives2 which may have better therapeutic efficacy. These are prepared through silylation method3, mercuri salt method4 and direct alkylation method5 of 5-FU. It was reported5 that the direct alkylation of 5-FU with saturated and allylic type halides under controlled conditions occur at N3 (3-) and N1 (1-) position respectively in contrast to alkylation of uracil where N1 alkylated products are obtained in both cases. The position of alkylation in 5-FU was determined, with analogy from uracil6, by the bathochromic shift in UV from the neutral pH to alkaline pH of the 3-substituted product compared to no such shift of the 1-substituted product.

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