4,6-Dihydroxy-2-methylpyrimidine-5-carbaldehyde (cas: 14160-85-1) belongs to pyrimidine derivatives. Pyrimidines are isomeric with two other forms of diazines: pyridazine, with the nitrogen atoms in the 1 and 2 positions; and pyrazine, with the nitrogen atoms in the 1 and 4 positions. 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.Application of 14160-85-1
Synthesis of pyrimidine-5-carboxaldehydes by the Reimer-Tiemann reaction was written by Wiley, Richard H.;Yamamoto, Yuzuru. And the article was included in Journal of Organic Chemistry in 1960.Application of 14160-85-1 The following contents are mentioned in the article:
Substituted pyrimidines, N:CR.N:CR1.CX:CR2 (I, X = H, R = OH. Me, OH, SH, SMe, OH, Me, H, H, OH, R1 = OH, OH, OH, OH, OH, Me, OH, OH, OH, OH, R2 = H, OH, Me, Me, Me, Me, Me, Me, H, OH) (II-XI) were submitted to the Reimer-Tiemann reaction by treatment 1 h. in dilute alc. with KOH and CHCl3 at 80° and neutralization of the precipitate K salts with AcOH to give the corresponding 5-carboxaldehydes I (X = CHO) (XII). The monohydroxylated pyrimidines V, VI, VII, and VIII did not precipitate the K salt and were isolated through a suitable derivative Data were tabulated for the isolated XII [pyrimidine, % yield of XII, and m.p. (solvent) given)]: XI, 42, 330° (H2O); II, 18, 304° (MeOH, H2O); III, 29, 300° (AcOH); IV, 14, -; V, 17, 300° (H2O); VI, 14, 300° (dilute alc.); VII, 26, -; VIII, 13, -. IX gave only 1.5% non-characterized derivative and no aldehyde or derivative was obtained from X. The data were consistent with the established difference in reactivity between IX and VIII, the less reactive nature of the pyrimidine nucleus than that of benzene, and the mechanism of the Reimer-Tiemann reaction. Various derivatives of XII were prepared and m.p. data listed [aldehyde, m.p. (solvent) of phenylhydrazone, dinitrophenylhydrazone, dimethylhydrazone, bis(2-hydroxyethyl)hydrazone, oxime, and semicarbazone of the corresponding XII given]: XI, 271-3° (AcOH), 301-2° (HCONMe2-alc.), 283-4° (MeOH), -, 250° (H2O),-; II, 298-300° (HCONMe2), 270-2° (MeOH), -, above 330° (MeOH), 260° (HCONMe2), 240° (reprecipitated from alk. solution); III, 240° (reprecipitated), above 330° (HCONMe2-H2O), 200° (EtOAc), -, -, 205° (reprecipitated); IV, -, -, 258-9° (MeOH), 320° (MeOH), 260° (MeOH),-; V, 276-7° (MeOH), -, 232-3° (MeOH), -, -, -; VI, 250-1° (MeOH), 283-4° (HCONMe2), 168-70° (MeOH), -, 228-9° (MeOH), 263° (reprecipitated); VII, 229-31° (MeOH), -, -, -, -, -; VIII, 277-9° (MeOH), 305° (HCONMe2), 192-3° (MeOH), -, 238-40° (MeOH), 265-6° (reprecipitated from alk. solution). CHCl3 (24 mL.) and 56 g. KOH in 60 mL. H2O added in 20 min. with stirring to 22.4 g. II and 11.2 g. KOH in 180 mL. 5:4 H2O-alc. at 80°, the mixture refluxed 1 h., the cooled mixture filtered from KCl, kept 10 h. at 20°, the precipitated K salt suspended in H2O, and neutralized with AcOH gave 8.6% XII (R = R1 = OH, R2 = H). The filtrate with PhNHNH2 gave 9.4% phenylhydrazone. XII (R = R1 = OH, R2 = Me) oxime (XIII) (0.5 g.) and 10 mL. Ac2O refluxed 30 min. and the hot filtered solution cooled to 20° gave 0.15 g. I (R = R1 = OH, R2 = Me, X = CN), m. above 330°, λ 273 mμ, also obtained (56%) by refluxing 0.5 g. XIII with 4.5 mL. POCl3, pouring the mixture onto ice, and recrystallizing from alc. XIII (0.7 g.) in 6 mL. POCl3 treated slowly with cooling with 3 mL. PhNMe2, the mixture refluxed 30 min., cooled, poured onto ice, extracted with Et2O, and the product recrystallized from ligroine (b. 60-80°) yielded 57% I (R = R1 = OH, R2 = Me, X = CN), m. 93-4°, converted by recrystallization from EtOH to I [R = Cl(EtO), R1 = EtO(Cl), R2 = Me, X = CN], m. 134-6°. The ease with which XIII was dehydrated suggested that the HO group and H atom were in the trans configuration. This study involved multiple reactions and reactants, such as 4,6-Dihydroxy-2-methylpyrimidine-5-carbaldehyde (cas: 14160-85-1Application of 14160-85-1).
4,6-Dihydroxy-2-methylpyrimidine-5-carbaldehyde (cas: 14160-85-1) belongs to pyrimidine derivatives. Pyrimidines are isomeric with two other forms of diazines: pyridazine, with the nitrogen atoms in the 1 and 2 positions; and pyrazine, with the nitrogen atoms in the 1 and 4 positions. 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.Application of 14160-85-1
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia