The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 2-ethylthioisonicotinamide》. Authors are Gustak, E.; Koruncev, D.; Gluncic, B..The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Recommanded Product: 148-51-6. Through the article, more information about this compound (cas:148-51-6) is conveyed.
2-Ethylisonicotinaldehyde diethylacetal (I), b14 125-8°, was prepared in 61% yield from EtBr 112.2, Mg 33, 2-ethyl-4-bromopyridine 62, tri-Et orthoformate 180, and NH4Cl 215 g. Hydrolysis of 15.3 g. I with 150 ml. 10% HCl gave 83% free aldehyde (II), b20 92-5°; hydrazone m. 46-8°; thiosemicarbazone m. 215-16°. Willgerodt reaction of 0.75 g. II with 0.16 g. S in 30 ml. pyridine and 20 ml. NH3 yielded 56.5% of 2-ethylthioisonicotinoylamide.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia