Tetrahedron

An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin-and pyrimidin-2-yl acetate

…, M Lamorlette, M Maudet, M Ménard, P Plé, G Pasquet…

Index: Morgentin, Remy; Jung, Frederic; Lamorlette, Maryannick; Maudet, Mickael; Menard, Morgan; Ple, Patrick; Pasquet, Georges; Renaud, Fabrice Tetrahedron, 2009 , vol. 65, # 4 p. 757 - 764

Full Text: HTML

Citation Number: 19

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 ...