The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation of 3-hydroxy-5-hydroxymethyl-2,4-dimethylpyridine (4-deoxyadermine)》. Authors are Wibaut, J. P.; Uhlenbroek, J. H.; Kooijman, E. C.; Kettenes, D. K..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).Synthetic Route of C8H12ClNO2. Through the article, more information about this compound (cas:148-51-6) is conveyed.
The preparation of 4-deoxyadermine (I) as described earlier (CA 38, 32849) was improved to give a total yield 15%. Ac2CH2 (25 g.) was slowly added to a refluxing solution of 21 g. NCCH2CONH2 in 150 ml. EtOH and 3 ml. piperidine to give 97% 2-hydroxy-3-cyano-4,6-dimethylpyridine (II), m. 294°, which on nitration with HNO3 (d. 1.52) in Ac2O at 45-50° gave a 5-nitro derivative (III) m. 268° in 70% yield. A mixture of 50 g. dry III and 65 g. PCl5 was treated with 30 ml. POCl3 and heated to 130°, to yield 71% 2,4-dimethyl-3-nitro-5-cyano-6-chloropyridine, m. 112-13° (EtOH), which was reduced by Pd-C in MeOH and aqueous HCl to give 70-5% 2,4-dimethyl-3-amino 5-aminomethylpyridine di-HCl salt monohydrate (IV), m. 310° (decomposition). The reaction of IV with Ba(NO2)2 and H2SO4 at 0°, and subsequent heating to 90° afforded 45% I, m. 264°.
There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Synthetic Route of C8H12ClNO2, and with the development of science, more effects of this compound(148-51-6) can be discovered.
Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia