N-3 alkylation of uracils with unprotected amino alcohols using the Mitsunobu reaction

[Display omitted] •An unprecedented Mitsunobu alkylation of uracils at N-3 with unprotected amino alcohols is described.•Substrate scope evaluation of the amino alcohol pro-electrophile is shown and discussed.•The scope appears limited to imidic scaffolds as the pro-nucleophiles. During our search f...

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Bibliographic Details
Published in:Tetrahedron letters 2018-01, Vol.59 (3), p.256-259
Main Authors: Lafitte, Guillaume, Beillard, Audrey, Chambon, Sandrine, Soulet, Catherine, Dumais, Laurence, Mouis, Grégoire, Fournier, Jean-François, Clary, Laurence, Bouix-Peter, Claire, Tomas, Loic, Harris, Craig S.
Format: Article
Language:English
Subjects:
CGRP (Calcitonin gene-related peptide)
Mitsunobu alkylation
Unprotected amino alcohols
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Summary:[Display omitted] •An unprecedented Mitsunobu alkylation of uracils at N-3 with unprotected amino alcohols is described.•Substrate scope evaluation of the amino alcohol pro-electrophile is shown and discussed.•The scope appears limited to imidic scaffolds as the pro-nucleophiles. During our search for novel CGRP antagonists, we had great difficulty in accessing one of our key motifs. Herein, we communicate how we solved the problem by an unprecedented Mitsunobu alkylation using unprotected amino alcohols.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.12.024