An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate
Rémy Morgentin
1
,
Frédéric Jung
1
,
Maryannick Lamorlette
1
,
Mickaël Maudet
1
,
Morgan Ménard
1
,
Patrick Plé
1
,
Georges Pasquet
1
,
F. Renaud
1
1
AstraZeneca, Centre de Recherches, Parc industriel Pompelle B.P. 1050, 51689 Reims cedex 2, France
|
Publication type: Journal Article
Publication date: 2009-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The synthesis of methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate and alkyl 2-(5-hydroxypyrimidin-2-yl)acetate is described. Methodology for an efficient access to 5-hydroxy-pyridin- and pyrimidin-2-yl acetate cores has been developed. Based on the difference in halogen reactivity, 5-bromo-2-chloropyridine and its pyrimidine analogue were functionalized judiciously by SNAr and palladium-catalyzed reactions. The outlined strategy provides a high-yielding route suitable for large-scale synthesis of these compounds as well as paves the way for a potential rapid access to other heterocyclic analogues.
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GOST
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Morgentin R. et al. An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate // Tetrahedron. 2009. Vol. 65. No. 4. pp. 757-764.
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Morgentin R., Jung F., Lamorlette M., Maudet M., Ménard M., Plé P., Pasquet G., Renaud F. An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate // Tetrahedron. 2009. Vol. 65. No. 4. pp. 757-764.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tet.2008.11.064
UR - https://doi.org/10.1016/j.tet.2008.11.064
TI - An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate
T2 - Tetrahedron
AU - Morgentin, Rémy
AU - Jung, Frédéric
AU - Lamorlette, Maryannick
AU - Maudet, Mickaël
AU - Ménard, Morgan
AU - Plé, Patrick
AU - Pasquet, Georges
AU - Renaud, F.
PY - 2009
DA - 2009/01/01
PB - Elsevier
SP - 757-764
IS - 4
VL - 65
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2009_Morgentin,
author = {Rémy Morgentin and Frédéric Jung and Maryannick Lamorlette and Mickaël Maudet and Morgan Ménard and Patrick Plé and Georges Pasquet and F. Renaud},
title = {An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate},
journal = {Tetrahedron},
year = {2009},
volume = {65},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.tet.2008.11.064},
number = {4},
pages = {757--764},
doi = {10.1016/j.tet.2008.11.064}
}
Cite this
MLA
Copy
Morgentin, Rémy, et al. “An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate.” Tetrahedron, vol. 65, no. 4, Jan. 2009, pp. 757-764. https://doi.org/10.1016/j.tet.2008.11.064.