N-alkylation With Alcohols For The Preparation Of 2-(N-alkylamino) Pyrimidines

A alkylation catalyzed by transition metal to form C-N bond was designed in this papert. The research includes explorations of C-N forming reactions for preparations of 2-(N-alkylamino)pyrimidine and the reaction mechanism. Further, this reaction will open up new horizon in organic synthesis and expand application of alcohols. This paper mainly contains three parts:Substrates for N-alkylation are synthesised and best conditions were found. Firstly, synthesis 5-phenyl-2-aminopyrinidine and 4,6-diphenyl-2-aminopyrinidine with Suzuki coupling reaction; Synthesis 5-phenoxy-2-aminopyrimidine with nucleophilic substitution reaction. Synthesis 2-aminoquinazoline,4-phenyl-2-aminoq-uinzoline,6-fluoro-2-aminoquin azoline with Ullmann Coupling reaction and in this section, we has developed a CuI/NaOH /p-xylene/120℃systerm, and the conversion rate has improved greatly with this systerm. All the substrates are characterized by 1H NMR.The N-alkylation of 2-aminoquinazoline with n-butanol was chosen as a model to explore the reaction condition and identify the optimal condition of [Cp*IrCl2]2/NaOH. And in this condition, explore the reaction of 2-animoquinazoline with other alcohols, while exporing the reaction of 2-aminoquinazoline derivatives and 2-amino pyrimidives derivatives with n-butanol in the above conditions. And a variety of target products were characterized by 1H NMR,13C NMR and HRMS.According to the study of references and the analysis of the reaction data, the reaction mechanism was explored and provide the foundation for the further expansion of this kind of "Hydrogen Borrowing Process" in organic synthesis.