Reaction of β-alkoxyvinyl α-ketoesters with acyclic NCN binucleophiles – scalable approach to novel functionalized pyrimidines
Tetrahedron 2019, 75 (25), 3472-3478
Stepaniuk O.; Rudenko T.; Vashchenko B.; Matvienko V.; Kondratov I.; Tolmachev A.; Grygorenko O.
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.