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On the reactivity of N ‐benzylpyrimidinium salts with nitrogen nucleophiles
Author(s) -
Dlugosz A.,
van der Plas H. C.,
Van Veldhuizen A.
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190231
Subject(s) - chemistry , hydrazine (antidepressant) , bromide , nucleophile , reactivity (psychology) , ammonia , medicinal chemistry , liquid ammonia , nitrogen , benzyl bromide , organic chemistry , labelling , pyrimidine , stereochemistry , catalysis , medicine , biochemistry , alternative medicine , chromatography , pathology
Treatment of the l‐benzyl salts of pyrimidine, 4,6‐dimethylpyrimidine, and 4‐ t ‐butylpyrimidine with liquid ammonia leads to debenzylation. The 1 H‐nmr spectroscopic evidence is presented that the initial step in the debenzylation of l‐benzyl‐4,6‐dimethylpyrimidinium bromide is the addition of the ammonia at C‐2, while with l‐benzyl‐4‐ t ‐butylpyrimidinium bromide the addition takes place at C‐6. It is proved by 15 N labelling that the debenzylation occurs according to the ANRORC mechanism. The above‐mentioned l‐benzylpyrimidinium bromides give with hydrazine, pyrazole, 3,5‐dimethylpyrazole and 3‐ t ‐butylpyrazole, respectively.