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. 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.SDS of cas: 69785-94-0
Pyrimidine derivatives. II. 2 was written by Naito, Takio;Inoue, Shoji. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.SDS of cas: 69785-94-0 This article mentions the following:
The 2,4-Cl(NCS) derivative (I) of 5-nitropyrimidine (II) (0.2 g.) in 30 cc. EtOH treated dropwise under stirring with 0.27 g. PhONa in EtOH, the solvent removed after 1 hr., and the residue in a little H2O extracted with C6H6 gave the 2,4-(PhO)2 derivative of II, m. 105°. I (1 g.) added to 50 cc. 28% NH4OH at 15° gave the 2,4-(H2N)2 derivative of II, identical with the product from NH3 on the 2,4-Cl2 derivative (III) of II [Isay, Ber. 39, 250(1906)]. Excess 10% alc. NH3 (or EtNH2 or PhNH2) added dropwise to 5 g. I in 50 cc. C6H6 yielded 4.2 g. 2,4-H2N(NCS) derivative (IV) of II, m. 209-10° (decomposition) [or 2,4-(EtNH)2 derivative of II, m. 170°, or 2,4-PhNH(NCS) derivative (V) of II, m. 199-200°]. Powd. I (4.3 g.) added to 1.6 g. (H2N)2CS in 60 cc. hot H2O, the mixture stirred 30-40 min., cooled, made alk. (at the neutral point the yellow 2,4-[H2NC(:NH)S]2 derivative of II appeared), and the hydrolyzed alk. solution decolorized, filtered, and acidified yielded the 2,4-(HS)2 derivative of II, m. 213° (decomposition), identical with the product from III treated with 2 moles (H2N)2CS or 4 moles KSH. IV (0.19 g.) (or 0.27 g. V) added to 20 cc. MeOH containing 0.05 g. Na, and the mixture stirred 2 hrs. at 0° yielded 0.14 g. 2,4-H2N(MeO) derivative of II, m. 2272 [or 0.23 g. 2,4-PhNH(MeO) derivative of II, m. 183°]. Similarly, with EtONa in place of MeONa 2 g. IV yielded 1-1.1 g. alkali-insoluble 2,4-H2N(EtO) derivative (VI) of II, m. 227°, and the alkali-soluble 2,4-H2N(HS) derivative (VII) of II, decompose without melting, whereas V gave the alkali-insoluble 2,4-PhNH(EtO) derivative of II, m. 150°, and the alkali-soluble 2,4-PhNH(HS) derivative of II, reduced (1 g.) (without crystallization) with alk. Na2S2O4 to 0.65 g. 2,4-PhNH(HS) derivative (VIII) of 5-aminopyrimidine, m. 218° (decomposition). VII (1 g.) similarly reduced yielded 0.6 g. 2,5-diamino-4-mercaptopyrimidine (IX), m. 235° (decomposition). VI (1.5 g.) in 30 cc. AcOH reduced by heating 2 hrs. at 60° with 1.5 g. Fe powder yielded 1 g. 2,5-diamino-4-ethoxypyrimidine, m. 128-9°. Similar reduction of 1.5 g. IV (or V) yielded 1.1 g. 2,5-(H2N)2 derivative (X) of thiazolo[5,4-d]pyrimidine (XI), m. above 270°, decompose above 270° [or 1.15 g. 2,5-H2N(PhNH) derivative (XII) of XI, m. 243°]. Heating 0.5 g. X 1 hr. on a water bath with 5 cc. 10% NAOH and acidifying the mixture with AcOH opened the thiazole ring and yielded 0.4 g. 2,4,5-H2N(RS)(H2NCONH) derivative (XIII) (R = H) of pyrimidine, decompose about 270° [EtBr on the K salt of XIII (R = H) gave XIII (R = Et), m. 223-4° (decomposition)], and this (1 g.) further hydrolyzed by heating 15 hrs. on a water bath with 20 cc. 15% NaOH, and acidifying the product gave IX, identical with the reduction product of VII above; IX (EtS in place of HS) m. 87°. XII (1 g.) hydrolyzed similarly yielded 0.5 g. VIII. Cyclization of VIII and IX was carried out by refluxing with (a) HCO2H or Ac2O, (b) BzCl, or (c) K methylxanthate to give N:C(NHR).N:CH.C:C.S.CR’:N (compound used, R, R’, method, hrs. of refluxing, m.p., g. yield from 1 g. given): IX, H, H, a (HCO2H), 2, 248-9°, 0.6; IX, H, Me, a (Ac2O), 3, 223°, 0.8; VIII, Ph, H, a (HCO2H), 3, 152°, 0.75; VIII, Ph, Ph, b, 3, 187°, 1.4; IX, H, SH, c, 15, above 300°, 1.05; VIII, Ph, SH, c, 15, 267-8°, 1.09. The K salts of the last 2 compounds in 70% EtOH heated 20 min. with EtBr and PhCH2Cl, resp. (preceding abstract), gave the 2,5-EtS(H2N) derivative and the 2,5-PhCH2S(PhNH) derivative of XI, m. 168° and 154°, in yields of 0.22 g. from 0.24 g. and 0.32 g. from 0.31 g., resp. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0SDS of cas: 69785-94-0).
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. 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.SDS of cas: 69785-94-0
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia