Diversification and Design of Novel Aniline-Pyrimidines via Sonogashira/Suzuki Cross Coupling Reactions Catalyzed by Novel CLPN-Pd

Abstract

Aniline-pyrimidines derivatives, especially Mepanipyrim are used as fungicides and obliging to control several diseases, particularly grey mould (Botrytis cinerea) of vegetables and vines. A series of novel Aniline-pyrimidines derivatives like Mepanipyrim have been synthesized by using novel strategy via Sonogashira/Suzuki cross-coupling reaction. High competence, novel and recyclable CLPN−Pd (cross-linked ploy(ionic liquid)s Nano gels) is used as a catalyst in this synthetic method which we recycled three times. Various characterization like XPS, DLS, XPA, X-rays, HNMR and CNMR have been done for confirmation of CLPN−Pd. For these two combined reactions we used a lower amount of catalyst, has advantages of wide substrate range, compatibility with multiple functional groups, and higher yields. In this novel technique of diversification two hetero aryl chlorides, 4-chloro-6-methyl-N-phenylpyrimidin-2-amine and -chloro-6-methyl-N-(p-tolyl) pyrimidin-2-amine with hetero phenyl acetylene and hetero aryl boronic acid delivered the subsequent compounds with reasonable to excellent 50 %–93 % yields. All the diversified compounds have been verified by various spectroscopic analysis such as 1HNMR, 13CNMR, and HR-MS spectral study. The analysis and preliminary conclusion provided some reference value for further development of this kind of research and applications in the future.