On amination of 2-bromo-4-phenylpyrimidine with potassium amide, 2-amino-4-phenylpyrimidine, β-amino-β-phenylacrylonitrile and 4-amino-l-cyano-2-phenyl-l-aza-1,3-butadiene are formed. 
 
2-Bromo-4-phenyl-[l,3-15N]-pyrimidine has been prepared and found to give on amination 2-amino-4-phenylpyrimidine. which contains the original 15N mainly in the exocyclic amino group. This is explained by a mechanism, involving an initial Addition of the Nucleophile to position 6, a subsequent Ring-Opening by fission of the N(1)-C(6) bond and Ring-Closure (SN(ANRORC)-mechanism).

The SN(ANRORC)-mechanism plays a key role in the reaction of 2-bromo-4-phenylpyrimidine with potassium amide, leading to the formation of 2-amino-4-phenylpyrimidine, -amino--phenylacrylon

Paper

On the occurrence of the SN(ANRORC)-mechanism in the reaction of 2-bromo-4-phenylpyrimidine with potassium amide in liquid ammonia†‡

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