82619-55-4Relevant articles and documents
On the Reactivity of N-Benzylpyrimidinium Salts with Nitrogen Nucleophiles (1,2)
Dlugosz, A.,van der Plas, H.C.,van Veldhuizen, A.
, p. 373 - 375 (2007/10/02)
Treatment of the 1-benzyl salts of pyrimidine, 4,6-dimethylpyrimidine, and 4-t-butylpyrimidine with liquid ammonia leads to debenzylation.The 1H-nmr spectroscopic evidence is presented that the initial step in the debenzylation of 1-benzyl-4,6-dimethylpyrimidinium bromide is the addition of the ammonia at C-2, while with 1-benzyl-4-t-butylpyrimidinium bromide the addition takes place at C-6.It is proved by 15N labelling that the debenzylation occurs according to the ANRORC mechanism.The above-mentioned 1-benzylpyrimidinium bromides give with hydrazine, pyrazole, 3,5-dimethylpyrazole and 3-t-butylpyrazole, respectively.