Re: ORGLIST: S-alkylation of 2-thiouracil

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From: by way of Joao Aires de Sousa (r.ragno$##$caspur.it)
Date: Wed Mar 19 1997 - 03:18:33 EST


On Tue, 18 Mar 1997 alihoyer$##$inet.uni-c.dk wrote:

> Dear Gianluca,
>
> What was the product of the reaction?
>

As I wrote in the original message, using many different alkyl- and
cycloalkylhalides the product was a 2-alkyl- or
2-cycloalkylthio-4-oxopirimidine (that's to say the tautomer of
2-thiouracil in which the hydrogen on the sulfur atom is substituted by an
alkyl or cycloalkyl group).
With cyclopropyl iodide the reation doesn't occur...

Gianluca "Blue Merlin" Sbardella

>
> Dear colleagues,
> > I've synthesized many 6-substituted-2-alkylthio-4-oxo-pyrimidines by
> > S-alkylation of 2-thiouracils with alkyl halides and potassium carbonate
> > in DMF, but when I tried to introduce the cyclopropyl group in the same
> > way (i.e. with cyclopropyl iodide) I failed. Do you have any suggestion?
> > I'll summarize to the list the answers I'll get.
> > Thank you in advance,
> >
> > Gianluca " Blue Merlin" Sbardella
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    * Dr. Gianluca Sbardella E-mail: r.ragno$##$caspur.it *
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