HSAB-driven chemoselective N 1-alkylation of pyrimidine bases and their 4-methoxy-or 4-acetylamino-derivatives

A Gambacorta, D Tofani, MA Loreto, T Gasperi…

Index: Gambacorta, Augusto; Tofani, Daniela; Loreto, Maria Antonietta; Gasperi, Tecla; Bernini, Roberta Tetrahedron, 2006 , vol. 62, # 29 p. 6848 - 6854

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Citation Number: 13

Abstract

The lithium salts of the conjugated bases of 4-methoxy-and 4-acetylamino-2 (1H)- pyrimidinones 1–3 undergo highly chemoselective N1-methylation or ethylation when treated with methyl-or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O2-attack. Under the same conditions, a similar but less ...