289-95-2 Usage
Uses
Different sources of media describe the Uses of 289-95-2 differently. You can refer to the following data:
1. Pyrimidine is a heterocyclic organic molecule present in many pharmaceutical and naturally derived compounds. Used in the synthesis and discovery of antiviral medication, such as in the case of HIV and HSV. Also used in the synthesis of potent inhibitors of 15-lipoxygenase in the reduction of the release of leukotrienes.
2. 1. It has no direct applications itself with its derivatives cytosine, uracil and thymine being important components of nucleic acid. Many drugs (such as sulfadiazine, trimethoprim and 6-mercaptopurine) contain pyrimidine ring.
2. Pyrimidine is widely used as pharmaceutical raw materials for the production of vitamin B, sulfadiazine, sulfadimidine, sulfamonomethoxine pyrimidine; pesticide raw materials, such as diazinon, pyrimidinol, blasticidin, bromacil, rumacil, crimidine, dodemorph, dimethirimol, ethirimol, bupirimate, pirazinon, pirimicarb, primicid, pirimiphos-methyl, polyoxin, pyramat, Pirimiphos-ethyl, etrimfos, triarimol, fenarimol and uracil, etc.; dye raw materials, for example, dyes with trihalogenated pyrimidine nucleus can react well with fiber and as reactive dyes, they have attracted people's attention.
3. It can be used as pharmaceutical intermediates, raw materials such as photosensitive agent
3. Pyrimidine is used as building block in chemical synthesis. Product Data Sheet
4. Pyrimidine was used to assess the extent of pyrimidine/purine asymmetry quantitatively. It was also used to study the photoinduced ion chemistry of the halogenated pyrimidines, a class of prototype radiosensitizing molecules.
Six-membered heterocyclic compounds
Pyridine, also known as "metadiazine", is a six-membered heteroaromatic ring compound containing two nitrogen atoms in the meta-position, being isomers with pyridazine and pyrazine. It has a molecular formula of C4H4N2 with the molecular weight being 80.09. It appears as colorless liquid or solid crystals with a pungent odor. It has a melting temperature of 20~22 ℃, boiling point of 123~124 °C and refractive index of 1.4998 (20 °C). It is easily soluble in water, ethanol and ether with weak alkaline and being capable of forming salts with acid. Its alkalinity is weaker than pyridine. It is also more difficult for it to participate into electrophilic substitution reaction than pyridine. It can only undergo bromination at the 5th position and is not capable of having nitrification and sulfonation reaction, but more prone to participate into nucleophilic substitution. Pyrimidine derivatives are widely found in nature. For example, vitamin B1, uracil, cytosine and thymine all contain pyrimidine structure. Its picrate salt appears as yellow needle-like crystals. It has a melting temperature of 156 °C. Owing to the presence of conjugated double bonds in the structure, pyrimidine has strong absorption capability on ultraviolet light. It is manufactured through phosphorus oxychloride oxidation of barbituric acid, followed by reduction through hydrogen iodide.
Nucleic acid contains three important pyrimidine derivatives, being an important base in nucleic acid, plays an important role in the body of organisms.
DNA mainly contains cytosine and thymine while RNA mainly contains cytosine and uracil, in some nucleic acids, there are also small amount of pyrimidine modified base, for example:
Sulfadiazine and its derivatives are commonly used antibacterial anti-inflammatory drugs.
The above information is edited by Andy Edwards of lookchem.
Pyrimidine base
Pyrimidine base is one of the chemical compositions of the nucleotides. It consists of carbon, nitrogen, hydrogen, oxygen and other elements. Pyrimidine bases include uracil, cytosine, and thymine, where uracil and cytosine constitute the bases in ribonucleic acid molecules while thymine and cytosine constitute bases in deoxyribonucleic acid molecules. Pyrimidine base has a strong absorption on ultraviolet in the wavelength of 250~280nm. The raw materials for its synthesis are derived from carbamoyl phosphate and aspartic acid. Pyrimidine base can also be metabolized into carbon dioxide, β-alanine and β amino-isobutyric acid and other substances. Some patients, due to congenital factors or taking certain drugs, can get pyrimidine alkali metabolic disorders, causing whey aciduria.
The functions of purine, pyrimidine and other substances
Purines and pyrimidines are essential heterocyclic nitrogen-containing compounds that used in nucleic acid metabolism in organisms (including humans) and are important substances in the formation of ribonucleic acid and deoxyribonucleic acid in cells. Purine, pyrimidine and ribose and phosphate can combine to form RNA; purine, pyrimidine and deoxyribose can bind to phosphate to produce DNA. DNA is the main chemical constituent of genes, which plays an important role in the transmission of genes (genetics); the main function of RNA is the regulation of intracellular protein synthesis. The final product of purine metabolism is mainly uric acid. Barley and malt contains 0.2% to 0.3% of the dry matter of nucleic acid. Upon the saccharification, the dry matter of nucleic acid can be subject to the degradation of various phosphatases to form nucleotides, nucleosides, purines and pyrimidine and many other degradation products, of which only purine and pyrimidine can enter into yeast cells to constitute ribonucleic acid, deoxyribonucleic acid, adenosine triphosphate and some coenzymes. Nucleotides are difficult to be absorbed. If the medium is lack of purine and pyrimidine, the cells have to rely on carbohydrates and amino acids for synthesis, thus consuming a lot of energy and influence the proliferation of yeast. In general, wort is not lack of the required purine and pyrimidine.
References: Chinese Medical Encyclopedia Editorial Board Editor; Guo Di editor in chief. Chinese Encyclopedia of Medicine ? fifty-seven pediatrics.
Preparation
1, take malondialdehyde and formamide as raw materials and have reaction upon heating; we can obtain pyrimidine.
2, it can be manufactured through the catalytic hydrogenation of 2, 4-dichloropyrimidine in the system.
3, use zinc powder to reduce 2, 4, 6-trichloropyrimidine, pyrimidine can be obtained.
4, the reaction between ethyl acetoacetate and amidine (below) can produce pyrimidine.
Fluorouracil
Fluorouracil is a pyrimidine antimetabolite. In the body, it is first converted into 5-fluoro-2-deoxyuridine nucleotides (FUdRP), causing inhibition of thymidylate synthase (TMPS), preventing the conversion of deoxyuridine nucleotide into thymidine, interfering with DNA synthesis and leading to cell damage and death. It has a stronger effect in the presence of leucovorin (CF) because FUdRP, FH4 and TMPS can form triple complexes making the active metabolite of drug bind more tightly with the enzyme, so addition of CF when applying will yield better efficacy, especially improving the efficacy upon being applied to colorectal cancer. This product is cell cycle-specific drugs with killing effects on proliferated cells at all stages. It is most sensitive to the S phase, and also has retardation effect on the G1/S border. Oral absorption is not complete, and the drug is easily inactivated upon liver metabolism. After intravenous infusion or arterial infusion, the blood concentration is relatively stable.
Fluorouracil has relative significant effect against choriocarcinoma and malignant mole. It also has certain curative effects on gastric cancer, colon cancer, rectum cancer, liver cancer, pancreatic cancer, breast cancer, ovarian cancer, cervical cancer, prostate cancer, bladder cancer, kidney cancer, lung cancer, head and neck cancer and skin cancer.
Chemical properties
It appears as colorless crystalline or liquid.
Chemical Properties
Colourless to pale yellow liquid
Definition
Different sources of media describe the Definition of 289-95-2 differently. You can refer to the following data:
1. One of a group of basic compounds
found in living matter. They may be isolated fol-
lowing complete hydrolysis of nucleic acids. They
include uracil, thymine, cytosine, and methylcy-
tosine. Thiamine is also a pyrimidine derivative.
Other pyrimidines such
2. A
simple nitrogenous organic molecule
whose ring structure is contained in the
pyrimidine bases cytosine, thymine, and
uracil, which are constituents of the nucleic
acids.
3. pyrimidine: An organic nitrogenousbase (see formula), sparinglysoluble in water, that gives rise to agroup of biologically important derivatives,notably uracil, thymine,and cytosine, which occur in nucleotidesand nucleic acids (DNA andRNA).
Check Digit Verification of cas no
The CAS Registry Mumber 289-95-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 9 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 289-95:
(5*2)+(4*8)+(3*9)+(2*9)+(1*5)=92
92 % 10 = 2
So 289-95-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2/c1-2-5-4-6-3-1/h1-4H
289-95-2Relevant articles and documents
Nickel-Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates
Daili, Farah,Ouarti, Abdelhakim,Pinaud, Marine,Kribii, Ibtihal,Sengmany, Stéphane,Le Gall, Erwan,Léonel, Eric
supporting information, p. 3452 - 3455 (2020/05/25)
A mild and useful nickel-catalyzed electrochemical phosphonylation of aryl and vinyl bromides is described. We show that alkyl H-phenylphosphinates can be coupled electrochemically with functionalized aryl and vinyl bromides using very simple conditions (Fe/Ni anode, bench-stable nickel pre-catalyst, undivided cell, galvanostatic electrolysis) to furnish the corresponding aryl and vinyl phosphinates in satisfactory to good yields. Couplings can also be applied to heteroaromatic bromides with some limitations like increased propensity to hydro-dehalogenation.
Flow hydrodediazoniation of aromatic heterocycles
R?der, Liesa,Nicholls, Alexander J.,Baxendale, Ian R.
, (2019/06/05)
Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system.
Infrared spectra of pyrazine, pyrimidine and pyridazine in solid argon
Breda,Reva,Lapinski,Nowak,Fausto
, p. 193 - 206 (2007/10/03)
The vibrational spectra of monomeric diazines (pyrazine, pyrimidine and pyridazine) isolated in solid argon and of the neat crystalline phase of these compounds, at 10 K, are reported and discussed. Full assignment of the spectra is presented, providing evidence that the assignments of several bands previously undertaken for the compounds under other experimental conditions (e.g., gas phase, neat liquid or solution) shall be reconsidered. The interpretation of the experimental data is supported by extensive DFT calculations performed with the B3LYP functional and the 6-311++G(d,p) basis set and by comparison with the anharmonic vibrational calculations reported by Boese and Martin [J.Phys.Chem. A, 108 (2004) 3085] and Berezin et al. [Russian J.Phys.Chem., 79 (2005) 425; Opt.Spectrosc., 97 (2004) 201]. Spectra/structure correlations were extracted from the data, enabling to conclude that, while the π-electron systems in both pyrazine and pyrimidine rings are strongly delocalized over all heavy-atoms, in pyridazine the canonical form with one CC and two CN double bonds strongly predominates. Finally, the UV-induced photoisomerization of matrix isolated monomeric pyrazine to pyrimidine is reported.
