The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetical and natural phellandrene》. Authors are Kondakoff, Iwan; Schindelmeiser, Iwan.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).Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. Through the article, more information about this compound (cas:148-51-6) is conveyed.
Compare Abstract, 1903, i, 845. tert.-Carvomenthyl chloride, obtained from tert.-carvomenthol, boils at 83.5-84.5° under 12 mm. pressure, has a sp. gr. 0.932 at 20°/4°, and forms tert.-carvomenthene, which boils at 174-176°, has a sp. gr. 0.811 at 20°/4°, and nD 1.45709. On treatment with bromine in strongly cooled light petroleum solution, this yields carvomenthene dibromide, which boils between 130° and 144° under 11 mm. pressure, has a sp. gr. 1.208 at 20°/4°, is optically inactive, and by alcoholic potassium hydroxide is converted into a hydrocarbon or mixture of hydrocarbons which must have the constitution (the original abstract includes an equation). This distils in two fractions: the larger boils at 175-180°, has a sp. gr. 0.825 at 20°/4°, and nD 1.46693; the smaller boils at 180-185°, has a sp. gr. 0.828 at 20°/4°, and nD 1.4673. The hydrocarbon is not identical therefore with natural phellandrene. Both fractions are optically inactive and give a red coloration with sulphuric acid in acetic acid solution. A specimen of phellandrene from Phellandrum aquaticum, which boils at 165-168°, has a sp. gr. 0.844 at 20°/4°, nD 1.47575, and [α]D +8°37′ at 20°, reacts with hydrochloric acid in acetic acid solution to form a dextrorotatory chloro-derivative, C10H17Cl, which melts at 110° and boils at 86° under 11 mm. pressure, and a dichloride, C10H18Cl2, which boils at 122.5-125° under 16 mm. pressure, and has a sp. gr. 1.006 at 20°/4° and nD 1.48516 at 20° (compare Pesci, Abstract, 1886, 1038).
There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Quality Control of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, and with the development of science, more effects of this compound(148-51-6) can be discovered.
Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia