5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. As nucleotides in DNA and RNA, pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Reference of 69785-94-0
Pyrimidine derivatives. I. Synthesis of thiazolo[5,4-d]-pyrimidines and related compounds. 1 was written by Takahashi, Torizo;Naito, Takio;Inoue, Shoji. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.Reference of 69785-94-0 This article mentions the following:
The title compounds were prepared as possible purine antagonists through derivatives of 4-thiocyano-5-nitropyrimidine (I) or 4-mercapto-5-aminopyrimidine (II) as intermediates. The 2,4-Cl2 derivative (III) of 5-nitropyrimidine (IV) (1.94 g.) in 5 cc. AcOH stirred 15 min. at 10° with 0.97 g. KSCN and the mixture poured into ice water yielded 1.84 g. 2-Cl derivative (V) of I, m. 141° (C6H6). V (2 g.) in 10 cc. MeOH or EtOH refluxed 5 hrs. on a water bath gave unexpectedly 5-nitrouracil, m. above 300°. However, 5 g. V added below 10° to 100 cc. EtOH containing 1.2 g. Na, the mixture stirred 2 hrs., the EtOH distilled, the residue diluted with H2O, and extracted with ether yielded from the extract 1.8-2.0 g. 2,4-(EtO)2 derivative (VI) of IV containing 2 moles EtONa, m. 45° (also prepared from III with EtONa), and from the acidified aqueous layer 2-2.5 g. 2,4-(EtO)(HS) derivative (VII) of IV, m. 133°. Similarly, 1.1 g. V added to 30 cc. MeOH containing 0.25 g. Na at 0° yielded 0.75 g. 2,4-(MeO)2 derivative (VIII) of IV, m. 95°. V (4.3 g.) in 60 cc. EtOH added dropwise at 0-5° to 1 mole EtSNa in 30 cc. EtOH gave after 2 hrs. at room temperature and concentration to 1/3 volume 2-(EtS) derivative (IX) of I, m. 131°. VI (3 g.) (or VIII) in 15 cc. AcOH heated 1 hr. at 60° on a water bath with 3 g. Fe powder, the filtrate from the mixture evaporated in vacuo, and the residue diluted with H2O and extracted with ether yielded 2.1 g. 2,4-(EtO)2 derivative of 5-aminopyrimidine (X), m. 64° [or the 2,4-(MeO)2 derivative of X, m. 89°. IX (0.3 g.) similarly reduced with Fe and AcOH yielded through ring closure 0.24 g. 2,5-H2N(EtS) derivative of thiazolo[5,4-d]-pyrimidine (XI), m. 123°; Ac derivative, m. 125-6°. VII (1.2 g.) in 5 cc. 10% NaOH stirred 15 min. at 50° with 5-7 g. Na2S2O4, cooled, and extracted with AcOEt yielded 0.7 g. 2-EtO derivative of II, m. 127°, and this (0.2 g.) refluxed 2 hrs. with 5 cc. HCO2H (or 5 cc. Ac2O), excess reagent removed in vacuo, and the residue made alk. and extracted with ether was cyclized to 0.09 g. 5-EtO derivative (XII) of XI, m. 95° [or 0.1 g. 2-Me derivative (XIII) of XII, m. 93°]. VII (0.5 g.) refluxed 15 hrs. with K methylxanthate (from 0.32 g. CS2 shaken with 0.3 g. KOH in 2 cc. H2O and 10 cc. MeOH), the mixture concentrated on a water bath, diluted with 5 cc. H2O, and neutralized with AcOH yielded 0.5 g. 2-HS derivative (XIV) of XII, m. about 234°, decompose above 280°. XIV (0.2 g.) refluxed 30 min. with 0.07 g. KOH in 15 cc. dilute EtOH and 0.11 g. EtBr (or 0.12 g. PhCH2Br), the solvent removed, and the resulting oil extracted with ether yielded 0.19 g. 2-EtS derivative of XII, m. 66° [or (omitting the ether extraction) 0.22 g. 2-PhCH2S derivative of XII, m. 102°]. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Reference of 69785-94-0).
5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. As nucleotides in DNA and RNA, pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Reference of 69785-94-0
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia