Barriers to rotation in dialkylaminopyrimidines

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Abstract
A number of 4-dialkylamino-pyrimidines (III), -quinazolines (II), and pyrido[3,2-d]pyrimidines (I), have been prepared, and their n.m.r. spectra studied in various solvents at room and at low temperatures. The barrier to rotation about the exocyclic C–N bond is not affected when the parent pyrimidine system (III) is annelated to a pyridine ring (I), but is substantially changed upon fusion to benzene (II). This finding is discussed in terms of a quantum-chemical all-valence electron approach.

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