Pyrimidines

Multi-Step Synthesis by Using Modular Flow Reactors: The Preparation of Yne-Ones and Their Use in Heterocycle Synthesis was written by Baxendale, Ian R.;Schou, Soeren C.;Sedelmeier, Joerg;Ley, Steven V.. And the article was included in Chemistry – A European Journal in 2010.Computed Properties of C16H13N3 This article mentions the following:

The palladium-catalyzed acylation of terminal alkynes gave yne-ones. The yne-ones were transformed into various heterocycles. The reactions are performed as a continuous-flow procedure by using a com. available pumping system and heated flow coils in combination with a suite of packed Omnifit glass tubes containing appropriate scavenger materials to ensure the quality of the final product. E.g., reaction of acid chloride 4-FC₆H₄COCl and terminal acetylene PhCCH, catalyzed by Pd(OAc)₂, gave 80% 1-(4-fluorophenyl)-3-phenylprop-2-yn-1-one. The yne-ones were used to prepare heterocycles. Thus, a hydrazine input stream was used to prepare pyrazoles in a single operation. In the experiment, the researchers used many compounds, for example, 4,6-Diphenylpyrimidin-2-amine (cas: 40230-24-8Computed Properties of C16H13N3).

4,6-Diphenylpyrimidin-2-amine (cas: 40230-24-8) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Computed Properties of C16H13N3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design was written by Wang, Linxiao;Zhang, Qian;Wang, Zhe;Zhu, Wufu;Tan, Ninghua. And the article was included in European Journal of Medicinal Chemistry in 2021.Safety of 4-(2-Chloropyrimidin-4-yl)morpholine This article mentions the following:

Using cheminformatics tools RDKit and literature investigation, four series of 24 thienopyrimidine I [X = C, C=O; Y = H, N(Me)₂, N(Et)₂] II [R = H, Me; R² = pyrrolidin-1-yl, 1-piperidyl, morpholino, indolin-1-yl, 3,4-dihydro-1H-isoquinolin-2-yl] III and N-methylpicolinamide derivatives IV [R² = pyrrolidin-1-yl, 1-piperidyl, morpholino, 3,4-dihydro-1H-isoquinolin-2-yl] substituted with pyrimidine were designed, synthesized and evaluated for activities against three cancer cell lines (MDA-MB-231, HCT116 and A549), TAK1 kinase and NF-κB signaling pathway. Almost all compounds I, II, III, IV showed selectivity toward the A549 cell lines and the most promising compound IV [R² = 1-piperidyl] could inhibit TAK1 kinase and NF-κB signaling pathway with the IC₅₀ values of 0.58 and 0.84μM. Moreover, IV [R² = 1-piperidyl] could induce cell cycle arrest of A549 cells at the G2/M checkpoint with 30.57% and induce apoptosis (34.94%) in a concentration-dependent manner. And western blot showed that compound IV [R² = 1-piperidyl] could inhibit TNF-α-induced IκBα phosphorylation, IκBα degradation, p65 phosphorylation and TAK1 phosphorylation, and reduce the expression of p65. The studies of docking, mol. dynamics, MM/PBSA and frequency anal. theor. supported the conclusions of the bioevaluation. In the experiment, the researchers used many compounds, for example, 4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0Safety of 4-(2-Chloropyrimidin-4-yl)morpholine).

4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0) 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. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Safety of 4-(2-Chloropyrimidin-4-yl)morpholine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Dynamic distribution and driving mechanisms of antibiotic resistance genes in a human-intensive watershed was written by Yang, Jun;Xiang, Jinyi;Xie, Yu;Yu, Kaifeng;Gin, Karina Yew-Hoong;Zhang, Bo;He, Yiliang. And the article was included in Water Research in 2022.Formula: C11H12N4O3S This article mentions the following:

Accelerated urbanization has promoted urban watersheds as important reservoirs of antibiotic resistance genes (ARGs); yet the biogeog. patterns and driving mechanisms of ARGs at the watershed scale remain unclear. Here, we examined the dynamic distribution of ARGs in a human-intensive watershed (including city, river and lake systems) over different seasons in a temperate region, as well as revealed the key factors shaping ARGs dynamics through structural equation models (SEMs). High diversity and abundance of ARGs were detected in sediments and surface water, with aminoglycoside, beta-lactamase and multidrug resistance genes dominating. PCoA showed distinct ARGs variations between the two phases. Seasonal changes and regional functions had significant impacts on the distribution patterns of ARGs. More diverse ARGs were detected in winter, while higher ARGs abundances were observed in spring and summer. The city system showed the highest level of ARGs contamination and was mainly derived from wastewater and human/animal feces based on SourceTracker anal. and ARGs indicators. Notably, watershed restoration could significantly mitigate the ARGs pollution status and improve biodiversity in the aquatic environment. Network anal. identified several hub ARGs and bacterial genera, which helped to infer potential bacterial hosts carrying ARGs. Furthermore, ARGs indicators provided insights to trace ARGs sources. SEMs indicated that bioavailable heavy metals and nutrients can greatly shape ARGs dynamics in regions with high-intensity human activities, while the microbial community and MGEs dominate the fate of ARGs in less human-impacted regions. More attention should be given to control heavy metals and nutrients to curb the spread of ARGs. Overall, this study highlights the environmental fate of ARGs and provides novel strategies to mitigate ARGs pollution in the human-intensive watershed. In the experiment, the researchers used many compounds, for example, 4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3Formula: C11H12N4O3S).

4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. Pyrimidine derivatives have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.Formula: C11H12N4O3S

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Practical Asymmetric Synthesis of a Non-Peptidic α_vβ₃ Antagonist was written by Keen, Stephen P.;Cowden, Cameron J.;Bishop, Brian C.;Brands, Karel M. J.;Davies, Antony J.;Dolling, Ulf H.;Lieberman, David R.;Stewart, Gavin W.. And the article was included in Journal of Organic Chemistry in 2005.Recommanded Product: 90905-32-1 This article mentions the following:

The development of a practical and highly convergent synthesis of an α_vβ₃ antagonist I is described. The two key fragments present in this compound, a chiral 3-aryl-5-oxopentanoic acid II and a tetrahydropyrido[2,3-b]azepine ring system III (R= Boc), were constructed independently and then coupled at a late stage using a Wittig reaction. The pyridoazepine moiety was prepared from N-Boc 6-chloro-2-aminopyridine via directed ortho-metalation/alkylation followed by in situ cyclization. A Suzuki reaction was then used to attach the propionaldehyde side-chain required for Wittig coupling. The coupling partner was prepared from asym. methanolysis of a 3-substituted glutaric anhydride followed by elaboration of the acid moiety to the requisite β-keto phosphorane. Using this route, kilogram quantities of the desired drug candidate were prepared In the experiment, the researchers used many compounds, for example, 2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1Recommanded Product: 90905-32-1).

2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.Recommanded Product: 90905-32-1

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Total Synthesis of (±)-Cylindrospermopsin was written by Xie, Chaoyu;Runnegar, Maria T. C.;Snider, Barry B.. And the article was included in Journal of the American Chemical Society in 2000.Recommanded Product: 59864-30-1 This article mentions the following:

The first total synthesis of the novel hepatotoxin (±)-cylindrospermopsin (I) has been accomplished in 20 steps from 4-methoxy-3-methylpyridine (II) in 3.5% overall yield. The substituted piperidine A ring III was generated stereospecifically by a four-step sequence using the addition of trimethylsilylethynylmagnesium bromide to II to give IV (Troc = CO₂CH₂CCl₃) and stereospecific addition of vinylcuprate to IV to form V. The reaction of diamine VI (R¹ = R² = H; TBDMS = SiMe₂CMe₃) with cyanogen bromide produced the cyclic guanidine C ring of VI (R¹R² = C:NH). The key step in the synthesis was bromination of ketone VII (Cbz = CO₂CH₂Ph), followed by hydrogenation to liberate the free guanidine, which underwent an intramol. S_N2 reaction to form the tetrahydropyrimidine ring B of VIII. Further hydrogenation reduced the ketone to yield 42% of VIII containing the fully functionalized tricyclic system and protected hydroxymethyluracil side chain of cylindrospermopsin. Hydrolysis of the pyrimidine in concentrated hydrochloric acid and selective monosulfation completed the synthesis of cylindrospermopsin. In the experiment, the researchers used many compounds, for example, 2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1Recommanded Product: 59864-30-1).

2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1) 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. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.Recommanded Product: 59864-30-1

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Influence of the C-5 substitution in polysubstituted pyrimidines on inhibition of prostaglandin E₂ production was written by Kolman, Viktor;Kalcic, Filip;Jansa, Petr;Zidek, Zdenek;Janeba, Zlatko. And the article was included in European Journal of Medicinal Chemistry in 2018.Application of 40230-24-8 This article mentions the following:

As a part of a broader structure-activity relationship study of substituted 2-aminopyrimidines, the influence of the C-5 substitution on inhibition of prostaglandin E2 (PGE2) production was studied. Thirty compounds were prepared starting from the corresponding 2-amino-4,6-dichloropyrimidines using Suzuki cross-coupling. It was shown previously that 2-amino-4,6-dichloropyrimidines with smaller C-5 substituent (hydrogen and methyl) were devoid of significant activity, while 5-Bu derivatives exhibited prominent potency. In this study, on the other hand, both monoaryl- and bisarylpyrimidines were potent inhibitors of PGE2 production regardless the length of the C-5 substituent (hydrogen, Me, n-butyl). Moreover, the shorter the C-5 substituent the higher potency to inhibit PGE₂ production was observed 2-Amino-4,6-diphenylpyrimidine was the best inhibitor of PGE2 production with IC₅₀ = 3 nM and no cytotoxicity. The most potent inhibitors deserve further preclin. evaluation as potential anti-inflammatory agents. In the experiment, the researchers used many compounds, for example, 4,6-Diphenylpyrimidin-2-amine (cas: 40230-24-8Application of 40230-24-8).

4,6-Diphenylpyrimidin-2-amine (cas: 40230-24-8) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Application of 40230-24-8

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Pyrimidine derivatives. V. 5 was written by Inoue, Shoji. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.Synthetic Route of C4H5N3O This article mentions the following:

Thiazolo[5,4-d]pyrimidine (I) and its 2-substituted derivatives are synthesized. The 4-HS derivative (II) of 5-aminopyrimidine (III) was 1st prepared from the 4-HO derivative (IV), the 6-Cl derivative (V), and the 6,4-Cl(HS) derivative (VI) of III. IV (1 g.) refluxed 8 hrs. with 3 g. P₂S₅ and 20 cc. xylene, the filtered solid from the cooled mixture dissolved in 20 cc. N NaOH, decolorized with C, and the filtrate neutralized with AcOH and extracted with AcOEt yielded 0.4-0.5 g. II, m. 207° (decomposition). The 4,6-Cl₂ derivative of 5-nitropyrimidine (5 g.) reduced with Fe powder and AcOH as above yielded 3 g. 4,6-Cl₂ derivative of III, m. 142°, which (5 g.) in 50 cc. EtOH heated 3 hrs. at 60° with the theoretical amount of KSH yielded 4.1 g. VI, m. above 300°, and this (1 g.) desulfurized with Raney Ni in NH₄OH (as was V in Part IV) yielded 0.2 g. V, m. 123° (decomposition). V (0.13 g.) in 5 cc. H₂O heated 2 hrs. at 60° with 0.2 g. KSH and the cooled mixture neutralized with AcOH yielded 0.1 g. II. VI (1 g.) refluxed 3 hrs. with 5 g. powd. Zn in 20 cc. H₂O and 3 cc. 28% NH₄OH, the filtrate from the mixture concentrated, neutralized, and extracted with AcOEt yielded 0.55 g. II. II was next cyclized as were similar compounds in the preceding abstracts (weight II, reagent, hrs. of refluxing, derivative of I formed, m.p., and g. yield given): 0.3 g., HCO₂H, 2, I, 144°, 0.1; 0.3 g., Ac₂O, 2, 2-Me, 77°, 0.16; 0.4 g., BzCl in C₅H₅N, 3, 2-Ph, 119-20°, 0.55; 0.2 g., K methylxanthate, 15, 2-HS (VII), 287° (decomposition), 0.21. The K salt of VII (0.2 g.) refluxed 30 min. with 0.12 g. PhCH₂Cl in 20 cc. 70% EtOH, the solvent distilled, the residue treated with 5 cc. N NaOH, and extracted with ether yielded 0.21 g. 2-PhCH₂S derivative of I, m. 101°. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Synthetic Route of C4H5N3O).

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. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Synthetic Route of C4H5N3O

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The preparation of some 4,6-disubstituted pyrimidine-5-carboxylic acids was written by Mehta, M. D.;Miller, D.. And the article was included in Journal of the Chemical Society in 1965.Computed Properties of C6H7BrN2O2 This article mentions the following:

4,6-Disubstituted pyrimidine-5-carboxylic acids have been prepared from 5-bromopyrimidines through the halogenmetal interconversion with n-butyllithium. When bromine and chlorine were both present in the pyrimidine nucleus, only the former underwent the interconversion reaction. Most of the acids were converted into derivatives through their acid chlorides. The reaction of 4,6-dimethoxypyrimidine with n-butyllithium gave a 2,5-dihydropyrimidine whose N.M.R. spectrum showed coupling between the C-2 and C-5 protons with the unusually large coupling constant of 5.5 c./s. This is discussed. In the experiment, the researchers used many compounds, for example, 5-Bromo-4,6-dimethoxypyrimidine (cas: 4319-77-1Computed Properties of C6H7BrN2O2).

5-Bromo-4,6-dimethoxypyrimidine (cas: 4319-77-1) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Computed Properties of C6H7BrN2O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Removal of antibiotics from milk via ozonation in a vortex reactor was written by Liu, Pengyun;Wu, Zhilin;Cannizzo, Francesca Tiziana;Mantegna, Stefano;Cravotto, Giancarlo. And the article was included in Journal of Hazardous Materials in 2022.COA of Formula: C11H12N4O3S This article mentions the following:

Antibiotics (ABX) residues occur frequently in milk, causing considerable wastage of medicated milk and serious economic losses, and making the issue a burden for the dairy industry. Improper disposal of medicated milk harms dairy production, animal welfare, and the environment. This work studies the use of ozonation in a vortex reactor for removing ceftiofur hydrochloride (CEF), sulfamonomethoxine sodium (SMM), marbofloxacin (MAR) and oxytetracycline (OTC) from milk. In terms of residual concentration, O₃ efficiency and the degradation kinetics of the various O₃-involving processes in the vortex reactor, ABX removal via ozonation is better using stronger vortexing, which induces hydrodynamic cavitation. CEF undergoes the fastest degradation, followed by SMM, MAR, and OTC. High ABX hydrophobicity favors ABX degradation via ozonation, O₃/H₂O₂, and O₃/Na₂S₂O₈. ABX oxidation by ^•OH at the O₃ gas-bubble/milk interface is the principle degradation pathway, except for MAR. ABX degradation follows pseudo-first-order kinetics and is affected by initial ABX concentration, O₃ concentration/flow rate, reaction temperature, and milk components to varying degrees. Under optimal ozonation conditions, ABX residues meet the maximum limits as set by the European Commission and no antimicrobial activity was observed The decontaminated milk was therefore suggested to be reused as calf food, animal feed, organic fertilizer, etc. In the experiment, the researchers used many compounds, for example, 4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3COA of Formula: C11H12N4O3S).

4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3) 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. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.COA of Formula: C11H12N4O3S

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Transformation kinetics and pathways of sulfamonomethoxine by UV/H₂O₂ in swine wastewater was written by Li, Yejin;Yang, Linyan;Chen, Xueming;Han, Yuefei;Cao, Guomin. And the article was included in Chemosphere in 2021.Synthetic Route of C11H12N4O3S This article mentions the following:

Sulfamonomethoxine (SMM), as one of the most predominant antibiotics in animal wastewater, is pending for effective control to minimize its environmental risks. Transformation kinetics and pathways of SMM by UV/H₂O2 in swine wastewater were systematically investigated in this study. Direct UV photolysis (as a dominant role) and •OH oxidation contributed to SMM degradation in UV/H₂O2 system. The less effective reaction rate of SMM in real wastewater than synthetic wastewater (0.1-0.17 vs. ∼0.2-1.5 min-1, despite higher H₂O2 dosage and extended reaction time) resulted mainly from the abundant presence of conventional contaminants (indicated by COD, a notable competitor of SMM) in real wastewater. SMM degradation benefited from higher H₂O2 dosage and neutral and weak alk. conditions. However, the effect of initial SMM concentration on SMM degradation in synthetic and real wastewater showed opposite trends, owning to the different probability of SMM mols. to interact with UV and H₂O2 in different matrixes. Carbonate had an inhibitory effect on SMM degradation by scavenging •OH and pH-variation induced effect, while nitrate promoted SMM degradation by generating more •OH. The removal efficiency of SMM in real wastewater reached 91% under the reaction conditions of H₂O2 of 10 mM, reaction time of 60 min, and pH 6.7-6.9. SMM degradation pathway was proposed as hydroxylation of benzene and pyrimidine rings, and secondary amine, and the subsequent cleavage of S-N bond. In the experiment, the researchers used many compounds, for example, 4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3Synthetic Route of C11H12N4O3S).

4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide (cas: 1220-83-3) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Synthetic Route of C11H12N4O3S

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia