Pyrimidine derivatives. V. 5 was written by Inoue, Shoji. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.Synthetic Route of C4H5N3O This article mentions the following:
Thiazolo[5,4-d]pyrimidine (I) and its 2-substituted derivatives are synthesized. The 4-HS derivative (II) of 5-aminopyrimidine (III) was 1st prepared from the 4-HO derivative (IV), the 6-Cl derivative (V), and the 6,4-Cl(HS) derivative (VI) of III. IV (1 g.) refluxed 8 hrs. with 3 g. P2S5 and 20 cc. xylene, the filtered solid from the cooled mixture dissolved in 20 cc. N NaOH, decolorized with C, and the filtrate neutralized with AcOH and extracted with AcOEt yielded 0.4-0.5 g. II, m. 207° (decomposition). The 4,6-Cl2 derivative of 5-nitropyrimidine (5 g.) reduced with Fe powder and AcOH as above yielded 3 g. 4,6-Cl2 derivative of III, m. 142°, which (5 g.) in 50 cc. EtOH heated 3 hrs. at 60° with the theoretical amount of KSH yielded 4.1 g. VI, m. above 300°, and this (1 g.) desulfurized with Raney Ni in NH4OH (as was V in Part IV) yielded 0.2 g. V, m. 123° (decomposition). V (0.13 g.) in 5 cc. H2O heated 2 hrs. at 60° with 0.2 g. KSH and the cooled mixture neutralized with AcOH yielded 0.1 g. II. VI (1 g.) refluxed 3 hrs. with 5 g. powd. Zn in 20 cc. H2O and 3 cc. 28% NH4OH, the filtrate from the mixture concentrated, neutralized, and extracted with AcOEt yielded 0.55 g. II. II was next cyclized as were similar compounds in the preceding abstracts (weight II, reagent, hrs. of refluxing, derivative of I formed, m.p., and g. yield given): 0.3 g., HCO2H, 2, I, 144°, 0.1; 0.3 g., Ac2O, 2, 2-Me, 77°, 0.16; 0.4 g., BzCl in C5H5N, 3, 2-Ph, 119-20°, 0.55; 0.2 g., K methylxanthate, 15, 2-HS (VII), 287° (decomposition), 0.21. The K salt of VII (0.2 g.) refluxed 30 min. with 0.12 g. PhCH2Cl in 20 cc. 70% EtOH, the solvent distilled, the residue treated with 5 cc. N NaOH, and extracted with ether yielded 0.21 g. 2-PhCH2S derivative of I, m. 101°. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Synthetic Route of C4H5N3O).
5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. Heterocyclic compounds bearing the pyrimidine core are of tremendous interest as they constitute an important class of natural and synthetic compounds exhibiting diverse useful biological activities that hold attractive potential for clinical translation as therapeutic agents in alleviation of a myriad of diseases. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Synthetic Route of C4H5N3O
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia