Reaction of β-alkoxyvinyl α-ketoesters with acyclic NCN binucleophiles – Scalable approach to novel functionalized pyrimidines
Two protocols for synthesis of series of low-molecular-weight di- and tri-substituted pyrimidines bearing a functional group at the 4th position, which rely on a base-mediated condensation of amidines or guanidines with β-alkoxyvinyl α-keto esters, have been developed. This approach allowed for multigram preparation of novel pyrimidine-4-carboxylates in 21–90% yield. The synthetic utility of these compounds was demonstrated by some standard functional group transformations providing promising building blocks for organic synthesis and drug discovery.
Stepaniuk, Oleksandr O.,Rudenko, Tymofii V.,Vashchenko, Bohdan V.,Matvienko, Vitalii O.,Kondratov, Ivan S.,Tolmachev, Andrey A.,Grygorenko, Oleksandr O.
supporting information
p. 3472 - 3478
(2019/05/17)
Studies on Pyrimidine Derivatives. XX. Synthetic Utility of Hydroxymethylpyrimidines and Related Compounds
The conversion of a hydroxymethyl group at the 2- or 4-position of simple pyrimidines to a chloromethyl, cyanomethyl, ethoxycarbonylmethyl, or formyl group is described.Various pyrimidines having an olefinic side chain were also synthesized via Witting reagents derived from chloromethylpyrimidines.Keywords - hydroxymethylation; chloromethylpyrimidine; cyanomethylpyrimidine; pyrimidinecarbaldehyde; Witting reaction