Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

Felix Kopp; Paul Knöchel

doi:10.1021/ol063136w

Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

Felix Kopp
, Paul Knöchel

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

Abstract

The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.

Original language	English (US)
Pages (from-to)	1639-1641
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/ol063136w
State	Published - Apr 26 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange",

abstract = "The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.",

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AU - Knöchel, Paul

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N2 - The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.

AB - The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.

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Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

Abstract

ASJC Scopus subject areas

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