Pyrimidines

Brown, D. J. published the artcilePyrimidines. I. Spectroscopic studies, Related Products of pyrimidines, the publication is Journal of the Chemical Society (1953), 331-7, database is CAplus.

Crude 2-chloropyrimidine (I) (2 g.) and NaOMe (from 0.5 g. Na and 25 ml. MeOH) refluxed 0.5 hr., cooled, saturated with CO₂, filtered, the filtrate concentrated in vacuo, the residue extracted with 40 ml. Et₂O, and the dried extract concentrated and distilled gave 0.83 g. 2-methoxypyrimidine (II), colorless liquid, b₁₅ 70-1°, n²⁰_D 1.5060. II (2.4 g.) and 20 ml. 15% Me₂NH-MeOH heated 1 hr. at 120°, NaOMe (from 0.4 g. Na in 20 ml. MeOH) added, and the mixture worked up as above (but without refluxing) gave 1.2 g. 2-(dimethylamino)pyrimidine (III), colorless hygroscopic liquid, b₁₇ 78-81°, n²²_D 1.5438. II and MeNH₂-EtOH similarly gave 2-(methylamino)pyrimidine (IV), b₁₄ 91-2°, m. 59-61° (from petr. ether). 4-Hydroxypyrimidine (V) (7 g.) and 25 ml. POCl₃ refluxed 25 min., cooled, extracted with six 15-ml. portions of petr. ether to remove the POCl₃, and the residue treated with MeOH gave as with II, 4-methoxypyrimidine (VI), colorless liquid, b₃₀ 69-70°. 2,4-Dimercaptopyrimidine (VII) (10.2 g.) and 60 ml. 25% aqueous Me₂NH heated 3 hrs. at 130°, evaporated, the residue treated with 200 ml. cold 0.5N HCl (VII was insoluble), the mixture filtered, and the filtrate adjusted to pH 3-4 gave 8.25 g. 4-dimethylamino-2-mercaptopyrimidine (VIII), m. 265-78° (decomposition), which, treated in 370 ml. boiling H₂O portionwise with 45 g. (wet weight) Raney Ni, refluxed 0.5 hr., filtered hot, the insoluble material washed with 100 ml. hot H₂O, the combined filtrates treated with 20 g. Raney Ni as above, filtered, the filtrate saturated with salt, extracted 15 hrs. with Et₂O, and the extracts concentrated and distilled gave 3.1 g. 4-(dimethylamino)pyrimidine (IX), b₅₀ 131-2°, m. about 40° 2-Mercapto-4-(methylamino)pyrimidine (12 g.) and Raney Ni as above gave 54% 4-(methylamino)pyrimidine (X), b₁₆ 142-4°, m, 69-72° (from petr. ether). 2-Aminopyrimidine (XI) (0.48 g.) and 1.5 ml. Ac₂O refluxed 1 hr., cooled, and 5 ml. Me₂CO added gave 0.45 g. 2-acetamidopyrimidine, colorless laths, m. 145-6.5° [from AcCH₂CHMe (XII)]. 4-Amino-5-cyanopyrimidine (XIII), m. 248-51° (decomposition) (7.4 g.), 55 ml. N KOH, and 225 ml. 3% H₂O₂ kept 1 hr. at 50-5°, the pH adjusted to 7, and the solution cooled gave 5.6 g. 4-amino-5-pyrimidinecarboxamide, colorless laths, m. 254-6° (from H₂O). XIII (1.9 g.) and 19 ml. 2.5N NaOH heated 1 hr. on the steam bath, the pH adjusted to 4, and the whole cooled gave 1.75 g. 4-amino-5 pyrimidinecarboxylic acid (XV), m. 278-81° (from H₂O); XIV (4.25 g.) and 40 ml. 2.5N NaOH gave as above 3.8 g. XV. XV (0.5 g.) added in portions to 5 g. Ph₂CO at 280, kept 5 min. at 280°, cooled to 100°, 25 ml. petr. ether (b. 100-20°) added, and the mixture cooled gave 0.1 g. 4-aminopyrimidine (XVI), m. 150° (from XII); 4-acetamido analog, colorless needles, m. 198-200° (from XII.). The pK_a (for 0.01M solution unless otherwise stated) at 20°, pH (as buffered), λ_maximum and log ε_maximum for the following compounds are reported: V, 1.69 ± 0.04 (or 8.60 ± 0.02), 13 (or 6.2), 227, 263 (or 223, 260), 4.06, 3.56 (or 3.87, 3.57); VI, 2.5 ± 0.2, 6.95 (0), 247-8 (227-8, 238), 3.53 (3.89, 386); XI (0.1M), 3.54, 7.0 (1), 224, 292 (221, 302-3), 4.13, 350 (4.17, 360); IV 3.82, 0.03, 7.0 (1), 234, 306-7 (228, 315), 4.23, 4.33 (4.23, 3.53); III, 3.96 ± 0.01, 7.0 (1), 243, 318 (235, 324-5), 4.26, 3.35 (4.24, 3.47); XVI (0.005M), 5.71, 13 (0), 233, 268-9 (246), 4.26, 3.72 (4.27); X, 6.12 ± 0.04, 9.0 (2.1), 242, 276-7 (254), 4.18, 3.54 (4.20); and IX, 6.35 ± 0.02, 9.3 (3.15), 250, 286 (262), 4.22, 3.56 (4.21). The infrared absorption curves for 2-hydroxypyrimidine, II, V, and VI in CCl₄ are shown; XI and XVI show the 2 strong bands characteristic of the H₂N group, proving that these 2 compounds exist in that form in this solvent. The various spectra are discussed.

Journal of the Chemical Society published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Tereshchenkov, A. G. published the artcileInteraction of chloramphenicol tripeptide analogs with ribosomes, HPLC of Formula: 186046-81-1, the publication is Biochemistry (Moscow) (2016), 81(4), 392-400, database is CAplus and MEDLINE.

Chloramphenicol amine peptide derivatives containing tripeptide fragments of regulatory “stop peptides”-MRL, IRA, IWP-were synthesized. The ability of the compounds to form ribosomal complexes was studied by displacement of the fluorescent erythromycin analog from its complex with E. coli ribosomes. It was found that peptide chloramphenicol analogs are able to bind to bacterial ribosomes. The dissociation constants were 4.3-10 μM, which is 100-fold lower than the corresponding values for chloramphenicol amine-ribosome complex. Interaction of the chloramphenicol peptide analogs with ribosomes was simulated by mol. docking, and the most probable contacts of “stop peptide” motifs with the elements of nascent peptide exit tunnel were identified.

Biochemistry (Moscow) published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C18H34N4O5S, HPLC of Formula: 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Metcalf, Gavin A. D. published the artcileAmplification-Free Detection of Circulating microRNA Biomarkers from Body Fluids Based on Fluorogenic Oligonucleotide-Templated Reaction between Engineered Peptide Nucleic Acid Probes: Application to Prostate Cancer Diagnosis, SDS of cas: 186046-81-1, the publication is Analytical Chemistry (Washington, DC, United States) (2016), 88(16), 8091-8098, database is CAplus and MEDLINE.

Highly abundant in cells, microRNAs (or miRs) play a key role as regulators of gene expression. A proportion of them are also detectable in biofluids making them ideal noninvasive biomarkers for pathologies in which miR levels are aberrantly expressed, such as cancer. Peptide nucleic acids (PNAs) are engineered uncharged oligonucleotide analogs capable of hybridizing to complementary nucleic acids with high affinity and high specificity. Herein, novel PNA-based fluorogenic biosensors have been designed and synthesized that target miR biomarkers for prostate cancer (PCa). The sensing strategy is based on oligonucleotide-templated reactions where the only miR of interest serves as a matrix to catalyze an otherwise highly unfavorable fluorogenic reaction. Validated in vitro using synthetic RNAs, these newly developed biosensors were then shown to detect endogenous concentrations of miR in human blood samples without the need for any amplification step and with minimal sample processing. This low-cost, quant., and versatile sensing technol. has been tech. validated using gold-standard RT-qPCR. Compared to RT-qPCR however, this enzyme-free, isothermal blood test is amenable to incorporation into low-cost portable devices and could therefore be suitable for widespread public screening.

Analytical Chemistry (Washington, DC, United States) published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, SDS of cas: 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Metcalf, Gavin A. D. published the artcileAmplification-Free Detection of Circulating microRNA Biomarkers from Body Fluids Based on Fluorogenic Oligonucleotide-Templated Reaction between Engineered Peptide Nucleic Acid Probes: Application to Prostate Cancer Diagnosis, Related Products of pyrimidines, the publication is Analytical Chemistry (Washington, DC, United States) (2016), 88(16), 8091-8098, database is CAplus and MEDLINE.

Highly abundant in cells, microRNAs (or miRs) play a key role as regulators of gene expression. A proportion of them are also detectable in biofluids making them ideal noninvasive biomarkers for pathologies in which miR levels are aberrantly expressed, such as cancer. Peptide nucleic acids (PNAs) are engineered uncharged oligonucleotide analogs capable of hybridizing to complementary nucleic acids with high affinity and high specificity. Herein, novel PNA-based fluorogenic biosensors have been designed and synthesized that target miR biomarkers for prostate cancer (PCa). The sensing strategy is based on oligonucleotide-templated reactions where the only miR of interest serves as a matrix to catalyze an otherwise highly unfavorable fluorogenic reaction. Validated in vitro using synthetic RNAs, these newly developed biosensors were then shown to detect endogenous concentrations of miR in human blood samples without the need for any amplification step and with minimal sample processing. This low-cost, quant., and versatile sensing technol. has been tech. validated using gold-standard RT-qPCR. Compared to RT-qPCR however, this enzyme-free, isothermal blood test is amenable to incorporation into low-cost portable devices and could therefore be suitable for widespread public screening.

Analytical Chemistry (Washington, DC, United States) published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Shrestha, Ritu published the artcileDual Peptide Nucleic Acid- and Peptide-Functionalized Shell Cross-Linked Nanoparticles Designed to Target mRNA toward the Diagnosis and Treatment of Acute Lung Injury, Formula: C39H35N5O8, the publication is Bioconjugate Chemistry (2012), 23(3), 574-585, database is CAplus and MEDLINE.

In this work, multifunctional biosynthetic hybrid nanostructures were prepared and studied for their potential utility in the recognition and inhibition of mRNA sequences for inducible nitric oxide synthase (iNOS), which are overexpressed at sites of inflammation, such as in cases of acute lung injury. Shell cross-linked knedel-like polymer nanoparticles (SCKs) that present peptide nucleic acids, for binding to complementary mRNAs, and cell penetrating peptides (CPPs), to gain cell entry, along with fluorescent labels and sites for radiolabeling, were prepared by a series of robust, efficient, and versatile synthetic steps that proceeded from monomers to polymers to functional nanoparticles. Amphiphilic block graft copolymers having combinations of methoxy- and thioacetyl-terminated poly(ethylene glycol) (PEG) and DOTA-lysine units grafted from the backbone of poly(acrylic acid) (PAA) and extending with a backbone segment of poly(octadecyl acrylate-co-decyl acrylate) (P(ODA-co-DA)) were prepared by a combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and chem. modification reactions, which were then used as the building blocks for the formation of well-defined SCKs decorated with reactive thiols accessible to the surface. Fluorescent labeling with Alexa Fluor 633 hydrazide was then accomplished by amidation with residual acrylic acid residues within the SCK shells. Finally, the PNAs and CPP units were covalently conjugated to the SCKs via Michael addition of thiols on the SCKs to maleimide units on the termini of PNAs and CPPs. Confirmation of the ability of the PNAs to bind selectively to the target iNOS mRNAs when tethered to the SCK nanoparticles was determined by in vitro competition experiments When attached to the SCKs having a hydrodynamic diameter of 60 ± 16 nm, the K_d values of the PNAs were ca. an order of magnitude greater than the free PNAs, while the mismatched PNA showed no significant binding.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C10H10O2, Formula: C39H35N5O8.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Shrestha, Ritu published the artcileDual Peptide Nucleic Acid- and Peptide-Functionalized Shell Cross-Linked Nanoparticles Designed to Target mRNA toward the Diagnosis and Treatment of Acute Lung Injury, Related Products of pyrimidines, the publication is Bioconjugate Chemistry (2012), 23(3), 574-585, database is CAplus and MEDLINE.

In this work, multifunctional biosynthetic hybrid nanostructures were prepared and studied for their potential utility in the recognition and inhibition of mRNA sequences for inducible nitric oxide synthase (iNOS), which are overexpressed at sites of inflammation, such as in cases of acute lung injury. Shell cross-linked knedel-like polymer nanoparticles (SCKs) that present peptide nucleic acids, for binding to complementary mRNAs, and cell penetrating peptides (CPPs), to gain cell entry, along with fluorescent labels and sites for radiolabeling, were prepared by a series of robust, efficient, and versatile synthetic steps that proceeded from monomers to polymers to functional nanoparticles. Amphiphilic block graft copolymers having combinations of methoxy- and thioacetyl-terminated poly(ethylene glycol) (PEG) and DOTA-lysine units grafted from the backbone of poly(acrylic acid) (PAA) and extending with a backbone segment of poly(octadecyl acrylate-co-decyl acrylate) (P(ODA-co-DA)) were prepared by a combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and chem. modification reactions, which were then used as the building blocks for the formation of well-defined SCKs decorated with reactive thiols accessible to the surface. Fluorescent labeling with Alexa Fluor 633 hydrazide was then accomplished by amidation with residual acrylic acid residues within the SCK shells. Finally, the PNAs and CPP units were covalently conjugated to the SCKs via Michael addition of thiols on the SCKs to maleimide units on the termini of PNAs and CPPs. Confirmation of the ability of the PNAs to bind selectively to the target iNOS mRNAs when tethered to the SCK nanoparticles was determined by in vitro competition experiments When attached to the SCKs having a hydrodynamic diameter of 60 ± 16 nm, the K_d values of the PNAs were ca. an order of magnitude greater than the free PNAs, while the mismatched PNA showed no significant binding.

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C48H47FeP, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Hsieh, Wei-Che published the artcileSynthesis of (R)- and (S)-Fmoc-protected diethylene glycol gamma PNA monomers with high optical purity, COA of Formula: C11H15N3O5, the publication is Journal of Organic Chemistry (2019), 84(3), 1276-1287, database is CAplus and MEDLINE.

A robust synthetic route has been developed for preparing optically pure, Fmoc-protected diethylene glycol-containing (R)- and (S)-γPNA monomers. The strategy involves the application of 9-(4-bromophenyl)-9-fluorenyl as a temporary, safety-catch protecting group for the suppression of epimerization in the O-alkylation and reductive amination steps. The optical purities of the final monomers were determined to be greater than 99.5% ee, as assessed by ¹⁹F-NMR and HPLC. The new synthetic methodol. is well-suited for large-scale monomer production, with most synthetic steps providing excellent chem. yields without the need for chromatog. purification other than a simple workup and precipitation

Journal of Organic Chemistry published new progress about 172405-16-2. 172405-16-2 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide, name is 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, and the molecular formula is C11H15N3O5, COA of Formula: C11H15N3O5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kolli, Murali Krishna published the artcilePd-PEPPSI-IPent^Cl: a new highly efficient ligand-free and recyclable catalyst system for the synthesis of 2-substituted indoles via domino copper-free Sonogashira coupling/cyclization, Synthetic Route of 1059705-07-5, the publication is New Journal of Chemistry (2017), 41(16), 8187-8195, database is CAplus.

A pyridine-containing decidedly resourceful Pd-N-heterocyclic carbene complex, Pd-PEPPSI-IPentCl (PEPPSI = pyridine enhanced precatalyst preparation, stabilization, and initiation), prepared and used as a first class recyclable catalytic system for the synthesis of 2-substituted indoles I [X = H, Boc; R¹ = H, 5-OMe, 6-i-Pr, 6-Cl, 5-NO₂, 5,7-di-NO₂; R² = Ph, 4-ClC₆H₄, 2-naphthyl, pyrimidin-5-yl, etc.] via domino copper-free Sonogashira coupling/cyclization. The catalyst showed a greater performance in the cascade reaction of various 2-bromo anilines with different terminal aromatic acetylenes under mild (60 °C) and green conditions (ethanol:water) even in the absence of a copper catalyst and an inert atm. It was confirmed that 0.1 mol% of the catalyst was sufficient, recyclable and could be reused up to six cycles.

New Journal of Chemistry published new progress about 1059705-07-5. 1059705-07-5 belongs to pyrimidines, auxiliary class Pyrimidine, name is 5-Ethynyl-2-methoxypyrimidine, and the molecular formula is C7H6N2O, Synthetic Route of 1059705-07-5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Hasanein, Ahmed A. published the artcileDFT calculations of amine-imine tautomerism in some pyrimidine derivatives and their 1:1 and 1:2 complexes with water, Category: pyrimidines, the publication is International Journal of Quantum Chemistry (2011), 111(15), 3993-4010, database is CAplus.

Amine-Imine tautomerization in 2-amino-pyrimidine (I), 2-amino-4,6-dichloropyrimidine (II), 2-amino-4,6-dimethylpyrimidine (III), and 2-amino-4,6-dimethoxypyrimidine (IV) and their 1:1 and 1:2 H-bonded complexes with water have been studied using the B3LYP/6-31++G** method. Optimum mol. geometries, electronic properties, and energetics of these systems have been discussed. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2011.

International Journal of Quantum Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Mussetta, Marie T. published the artcileConfigurations of 4-amino- and of 4-acetylaminopyrimidines and their derivatives, Safety of N,N-Dimethylpyrimidin-4-amine, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1973), 277(24), 1279-82, database is CAplus.

Dipole moments for pyrimidine, 4-aminopyrimidine (I), and 9 N-substituted I were measured in benzene or dioxane and were interpreted in relation to preferential conformations and interactions between the amino and adjacent ring N atoms.

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Safety of N,N-Dimethylpyrimidin-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia