Aminolysis of Pyrimidines Containing a Leaving Group at C-2 Different from Halogen

As one can see from Table IL5, the compounds with X = SCH3, SO2CH3, and SCN react with high percentages of participation of the Sn(ANRORC) process (73-90%) in the amide-induced aminolysis, while for X = CN, 

Percentages of Sn(ANRORC) Participation IN THE Amination of 2-Substituted-4-phenylpyrimidine by Potassium Amide/Liouid Ammonia 

There has been an attempt to correlate that fraction of the 2-substituted 4-phenylpyrimidines that takes part in the Sn(ANRORC) process (Xanrorc) and the inductive and resonance effects of the substituents, present in the substrate on position 2 (see Table II.6). (85T237). 

For that purpose the Swain nonresonance field constants F and resonance constants R were used (68JA4328). Xanrorc was calculated from % (chemical yield)/100 X %Sn(ANRORC)/100. The Xanrorc of the thiocyanate and the sulfonylphenyl are not included in Table II.6, since the F and R values are unknown. The 2-sulfonylmethyl substituent is also not included, as the F and R values of the conjugate base (the species present in this strong medium) are unknown. 

Based on this set of (limited) data a correlation was established, as given in the following equation  

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