88511-48-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrimidinecarboxamide (6CI,7CI,9CI) is used as a therapeutic agent for its potential anti-cancer properties. It has been studied for its ability to target and inhibit the growth of cancer cells, making it a promising candidate for cancer treatment.
Used in Genetic Research:
As a nucleobase found in DNA and RNA, 2-Pyrimidinecarboxamide (6CI,7CI,9CI) is used in genetic research to understand the fundamental mechanisms of genetic information storage and transmission. Its role in the genetic code and nucleic acid synthesis is essential for advancing our knowledge of genetics and molecular biology.
Used in Drug Development:
2-Pyrimidinecarboxamide (6CI,7CI,9CI) is utilized in drug development for its potential applications in treating various diseases beyond cancer. Its unique chemical structure and interactions with other molecules make it a valuable compound for the design and development of new therapeutic agents.

InChI:InChI=1/C5H5N3O/c6-4(9)5-7-2-1-3-8-5/h1-3H,(H2,6,9)

Upstream product

• 38275-60-4 5-bromo-pyrimidine-2-carboxylic acid amide 
• 14080-23-0 2-cyanopyrimidine 
• 404-71-7 1-fluoro-3-isocyanatobenzene 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 89581-38-4 5-bromopyrimidine-2-carboxylic acid methyl ester 

Downstream Products

• 14080-23-0 2-cyanopyrimidine 
• 91091-16-6 N-phenyl-pyrimidine-2-carboximidic acid amide 
• 90993-49-0 (Z)-N'-hydroxy-pyrimidine-2-carboxamidine 
• 45695-56-5 pyrimidine-2-carboxamidine 

Relevant academic research and scientific papers

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

Arene-ruthenium(II)-phosphine complexes: Green catalysts for hydration of nitriles under mild conditions

Three new arene-ruthenium(II) complexes were prepared by treating [{RuCl(μ-Cl)(η6-arene)}2] (η6-arene = p-cymene) dimer with tri(2-furyl)phosphine (PFu3) and 1,3,5-triaza-7-phosphaadamantane (PTA), respectively to obtain [RuCl2(η6-arene)PFu3] [Ru]-1, [RuCl(η6-arene)(PFu3)(PTA)]BF4 [Ru]-2 and [RuCl(η6-arene)(PFu3)2]BF4 [Ru]-3. All the complexes were structurally identified using analytical and spectroscopic methods including single-crystal X-ray studies. The effectiveness of resulting complexes as potential homogeneous catalysts for selective hydration of different nitriles into corresponding amides in aqueous medium and air atmosphere was explored. There was a remarkable difference in catalytic activity of the catalysts depending on the nature and number of phosphorus-donor ligands and sites available for catalysis. Experimental studies performed using structural analogues of efficient catalyst concluded a structural-activity relationship for the higher catalytic activity of [Ru]-1, being able to convert huge variety of aromatic, heteroaromatic and aliphatic nitriles. The use of eco-friendly water as a solvent, open atmosphere and avoidance of any organic solvent during the catalytic reactions prove the reported process to be truly green and sustainable.

Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane-Water

The catalytic nitrile hydration (amide formation) in a copper iodide/cesium carbonate/1,8-diazabicyclo[5.4.0]undec-7-ene/nitromethane-water system is described. The protocol is robust and reliable; it can be applied to a broad range of substrates with high chemoselectivity.

A Brevibacterium process for synthesizing amide

The invention discloses a method for synthesizing amide through nitrile hydrolysis. The method comprises the following steps: adding nitrile, acetaldoxime, water, a water-soluble rhodium complex to a reaction vessel, and cooling to room temperature after reaction of a reaction mixture for several hours at the temperature of 50-80 DEG C; and adding ethyl acetate for extraction so as to obtain an organic layer, and carrying out rotary evaporation to remove a solvent, thus obtaining a target product. Compared with a method for synthesizing amide through nitrile hydrolysis by using oxime as a water source in a transition metal catalysis process, the method has the advantages that a used catalyst is low in loading and does not contain a phosphine ligand seriously polluting environments, synthesis can be performed in air, and nitrogen protection is not needed; and therefore, the method meets the green chemistry requirements and has a wide development prospect.

Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity.

Substrate-Specific Heterogeneous Catalysis of CeO2 by Entropic Effects via Multiple Interactions

Achieving complete substrate specificity through multiple interactions like an enzyme is one of the ultimate goals in catalytic studies. Herein, we demonstrate that multiple interactions between the CeO2 surface and substrates are the origin of substrate-specific hydration of nitriles in water by CeO2, which is exclusively applicable to the nitriles with a heteroatom (N or O) adjacent to the α-carbon of the CN group but is not applicable to the other nitriles. Kinetic studies reveal that CeO2 reduces the entropic barrier (TΔS?) for the reaction of the former reactive substrate, leading to 107-fold rate enhancement compared with the latter substrate. Density functional theory (DFT) calculations confirmed multiple interaction of the reactive substrate with CeO2, as well as preferable approximation and alignment of the nitrile group of the substrate to the active OH group on CeO2 surface. This can lead to the reduction of the entropic barrier. This is the first example of an entropy-driven substrate-specific catalysis of a nonporous metal oxide surface, which will provide a new design strategy for enzyme-inspired synthetic catalysts.

Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide

A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.

Exploring rhodium(I) complexes [RhCl(COD)(PR3)] (COD = 1,5-cyclooctadiene) as catalysts for nitrile hydration reactions in water: The aminophosphines make the difference

Several rhodium(I) complexes, [RhCl(COD)(PR3)], containing potentially cooperative phosphine ligands, have been synthesized and evaluated as catalysts for the selective hydration of organonitriles into amides in water. Among the different phosphines screened, those of general composition P(NR 2)3 led to the best results. In particular, complex [RhCl(COD){P(NMe2)3}] was able to promote the selective hydration of a large range of nitriles in water without the assistance of any additive, showing a particularly high activity with heteroaromatic and heteroaliphatic substrates. Employing this catalyst, the antiepileptic drug rufinamide was synthesized in high yield by hydration of 4-cyano-1-(2,6- difluorobenzyl)-1H-1,2,3-triazole. For this particular transformation, complex [RhCl(COD){P(NMe2)3}] resulted more effective than related ruthenium catalysts.

Ceria-catalyzed conversion of carbon dioxide into dimethyl carbonate with 2-cyanopyridine

DMC run: Carbon dioxide can be converted into dimethyl carbonate in a reaction system involving 2-cyanopyridine as a dehydration agent, catalyzed by CeO2. Regeneration of the coproduct 2-picolinamide can be achieved over a Na2O/SiO2 catalyst. As a whole, the system servest to react carbon dioxide with methanol to produce dimethyl carbonate. Copyright

Enzymatic Hydrolysis of Heterocyclic Nitriles

Chemoselective hydrolysis of heterocyclic nitriles can be achieved by an easy to use immobilized biocatalyst prepared from Rhodococcus sp.Pyrimidine-2-carbonitrile (2a) and 3-chloropyridazine-4-carbonitrile (4a) were converted into the corresponding amides while from 2-ethoxycarbonyl-4-pyridinecarbonitrile (1a), 6-methylpyridazine-3-carbonitrile (3a), 3-chloropyridazine-4-carbonitrile (4a), 3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carbonitrile (8a), indole-3-carbonitrile (9a), and indole-3-ylacetonitrile (10a) the acids were formed.