Pyrimidine reactions. IX. The amination of chloropyrimidines with branched alkylamines and Di-n-alkylamines

Abstract

The reactions of 2-chloro-4,6-dimethylpyrimidine and 4-chloro-2,6-dimethylpyrimidine with some branched-alkyl- and dialkyl-amines have been followed from 30° to 70° in the absence of solvent. At comparable temperatures, alkylamines with β- or γ-branching approximated in reactivity to n-alkylamines, whereas those with α-branching and the di-n-alkylamines had only about 5% of the above reactivity; t-butylamine with two a-branches had but 0.1% of the reactivity of n-butylamine. Optimum conditions of time and temperature, calculated from these measurements, have been used to prepare 16 new alkylaminopyrimidines in good yield.