Tag: 100-200

Four products from the cyanoacetylation of pyrimidines: hydrogen-bonded dimers, π-stacked hydrogen-bonded chains and hydrogen-bonded chains of edge-fused rings was written by Trilleras, Jorge;Low, John N.;Cobo, Justo;Marchal, Antonio;Glidewell, Christopher. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2008.Category: pyrimidines This article mentions the following:

The mols. of 2-[6-amino-3-methyl-2-(methylsulfanyl)-4-oxo-3,4-dihydropyrimidin-5-ylcarbonyl]acetonitrile, C₉H₁₀N₄O₂S, (I), are linked in pairs by N-H···O hydrogen bonds to form cyclic centrosym. R₂²(4) dimers. Similar dimers formed by 2-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-ylcarbonyl)acetonitrile, C₉H₁₀N₄O₃, (II), are reinforced by paired N-H···N hydrogen bonds and linked into chains of rings by C-H···O hydrogen bonds. The mols. of 2-cyano-N-[6-methoxy-2-(methylsulfanyl)pyrimidin-4-yl]acetamide, C₉H₁₀N₄O₂S, (III), are linked into simple C(6) chains by an N-H···N hydrogen bond, and the chains are weakly linked into sheets by a π-π stacking interaction. A combination of one two-center N-H···N hydrogen bond and one three-center C-H···(N,O) hydrogen bond links the mols. of 2-cyano-N-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamide, C₈H₇ClN₄OS, (IV), into a chain of alternating edge-fused R₂¹(6) and R₁²(6) rings. The crystal structures reported in this study, and those of some related examples from the recent literature, show a wide variation in hydrogen-bonded aggregation consequent upon rather small changes in mol. constitution. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Category: pyrimidines).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Drugs having the pyrimidine motif have manifested to exhibit gratifying biological activity like anticancer, antiviral, anti-inflammatory, antibacterial, and antihypertensive activities.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Pyrimidine derivatives. I. Synthesis of thiazolo[5,4-d]-pyrimidines and related compounds. 1 was written by Takahashi, Torizo;Naito, Takio;Inoue, Shoji. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.Reference of 69785-94-0 This article mentions the following:

The title compounds were prepared as possible purine antagonists through derivatives of 4-thiocyano-5-nitropyrimidine (I) or 4-mercapto-5-aminopyrimidine (II) as intermediates. The 2,4-Cl₂ derivative (III) of 5-nitropyrimidine (IV) (1.94 g.) in 5 cc. AcOH stirred 15 min. at 10° with 0.97 g. KSCN and the mixture poured into ice water yielded 1.84 g. 2-Cl derivative (V) of I, m. 141° (C₆H₆). V (2 g.) in 10 cc. MeOH or EtOH refluxed 5 hrs. on a water bath gave unexpectedly 5-nitrouracil, m. above 300°. However, 5 g. V added below 10° to 100 cc. EtOH containing 1.2 g. Na, the mixture stirred 2 hrs., the EtOH distilled, the residue diluted with H₂O, and extracted with ether yielded from the extract 1.8-2.0 g. 2,4-(EtO)₂ derivative (VI) of IV containing 2 moles EtONa, m. 45° (also prepared from III with EtONa), and from the acidified aqueous layer 2-2.5 g. 2,4-(EtO)(HS) derivative (VII) of IV, m. 133°. Similarly, 1.1 g. V added to 30 cc. MeOH containing 0.25 g. Na at 0° yielded 0.75 g. 2,4-(MeO)₂ derivative (VIII) of IV, m. 95°. V (4.3 g.) in 60 cc. EtOH added dropwise at 0-5° to 1 mole EtSNa in 30 cc. EtOH gave after 2 hrs. at room temperature and concentration to 1/3 volume 2-(EtS) derivative (IX) of I, m. 131°. VI (3 g.) (or VIII) in 15 cc. AcOH heated 1 hr. at 60° on a water bath with 3 g. Fe powder, the filtrate from the mixture evaporated in vacuo, and the residue diluted with H₂O and extracted with ether yielded 2.1 g. 2,4-(EtO)₂ derivative of 5-aminopyrimidine (X), m. 64° [or the 2,4-(MeO)₂ derivative of X, m. 89°. IX (0.3 g.) similarly reduced with Fe and AcOH yielded through ring closure 0.24 g. 2,5-H₂N(EtS) derivative of thiazolo[5,4-d]-pyrimidine (XI), m. 123°; Ac derivative, m. 125-6°. VII (1.2 g.) in 5 cc. 10% NaOH stirred 15 min. at 50° with 5-7 g. Na₂S₂O₄, cooled, and extracted with AcOEt yielded 0.7 g. 2-EtO derivative of II, m. 127°, and this (0.2 g.) refluxed 2 hrs. with 5 cc. HCO₂H (or 5 cc. Ac₂O), excess reagent removed in vacuo, and the residue made alk. and extracted with ether was cyclized to 0.09 g. 5-EtO derivative (XII) of XI, m. 95° [or 0.1 g. 2-Me derivative (XIII) of XII, m. 93°]. VII (0.5 g.) refluxed 15 hrs. with K methylxanthate (from 0.32 g. CS₂ shaken with 0.3 g. KOH in 2 cc. H₂O and 10 cc. MeOH), the mixture concentrated on a water bath, diluted with 5 cc. H₂O, and neutralized with AcOH yielded 0.5 g. 2-HS derivative (XIV) of XII, m. about 234°, decompose above 280°. XIV (0.2 g.) refluxed 30 min. with 0.07 g. KOH in 15 cc. dilute EtOH and 0.11 g. EtBr (or 0.12 g. PhCH₂Br), the solvent removed, and the resulting oil extracted with ether yielded 0.19 g. 2-EtS derivative of XII, m. 66° [or (omitting the ether extraction) 0.22 g. 2-PhCH₂S derivative of XII, m. 102°]. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Reference of 69785-94-0).

5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. 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.Reference of 69785-94-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Discovery, synthesis, selectivity modulation and DMPK characterization of 5-azaspiro[2.4]heptanes as potent orexin receptor antagonists was written by Stasi, Luigi Piero;Artusi, Roberto;Bovino, Clara;Buzzi, Benedetta;Canciani, Luca;Caselli, Gianfranco;Colace, Fabrizio;Garofalo, Paolo;Giambuzzi, Silvia;Larger, Patrice;Letari, Ornella;Mandelli, Stefano;Perugini, Lorenzo;Pucci, Sabrina;Salvi, Matteo;Toro, PierLuigi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Reference of 16879-39-3 This article mentions the following:

Starting from an orexin 1 receptor selective antagonist 4,4-disubstituted piperidine series, a novel potent 5-azaspiro[2.4]heptane dual orexin 1 and orexin 2 receptor antagonist class has been discovered. SAR and pharmacokinetic optimization of this series is herein disclosed. Lead compound I exhibits potent activity against orexin 1 and orexin 2 receptors along with low cytochrome P 450 inhibition potential, good brain penetration and oral bioavailability in rats. In the experiment, the researchers used many compounds, for example, 2-Bromo-4,6-dimethylpyrimidine (cas: 16879-39-3Reference of 16879-39-3).

2-Bromo-4,6-dimethylpyrimidine (cas: 16879-39-3) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. 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.Reference of 16879-39-3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Discovery of potent LPA₂ (EDG4) antagonists as potential anticancer agents was written by Beck, Hilary P.;Kohn, Todd;Rubenstein, Steven;Hedberg, Christine;Schwandner, Ralf;Hasslinger, Kerstin;Dai, Kang;Li, Cong;Liang, Lingming;Wesche, Holger;Frank, Brendon;An, Songhzu;Wickramasinghe, Dineli;Jaen, Juan;Medina, Julio;Hungate, Randall;Shen, Wang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Safety of 4-Chloro-7-methylthieno[3,2-d]pyrimidine This article mentions the following:

The LPA₂ protein is overexpressed in many tumor cells. We report the optimization of a series of LPA₂ antagonists using calcium mobilization assay (aequorin assay) that led to the discovery of the first reported inhibitors selective for LPA₂. Key compounds were evaluated in vitro for inhibition of LPA₂ mediated Erk activation and proliferation of HCT-116 cells. These compounds could be used to evaluate the benefits of LPA₂ inhibition both in vitro and in vivo. In the experiment, the researchers used many compounds, for example, 4-Chloro-7-methylthieno[3,2-d]pyrimidine (cas: 175137-21-0Safety of 4-Chloro-7-methylthieno[3,2-d]pyrimidine).

4-Chloro-7-methylthieno[3,2-d]pyrimidine (cas: 175137-21-0) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Safety of 4-Chloro-7-methylthieno[3,2-d]pyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Studies of pyrimidine derivatives. XXXVIII. Cross-coupling reaction of N-heteroaryl iodides with ethoxycarbonylmethylzinc bromide in the presence of palladium catalyst was written by Yamanaka, Hiroshi;Annaka, Masayuki;Kondo, Yoshinori;Sakamoto, Takao. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Recommanded Product: 2-Bromo-4,6-dimethylpyrimidine This article mentions the following:

In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatskii reagent) to give Et 4,6-dimethyl-2-pyrimidineacetate and Et 2,6-dimethyl-4-pyrimidineacetate, resp. In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides. In the experiment, the researchers used many compounds, for example, 2-Bromo-4,6-dimethylpyrimidine (cas: 16879-39-3Recommanded Product: 2-Bromo-4,6-dimethylpyrimidine).

2-Bromo-4,6-dimethylpyrimidine (cas: 16879-39-3) 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.Recommanded Product: 2-Bromo-4,6-dimethylpyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Cinchona alkaloid thiourea-catalyzed one-pot synthesis and bioselective activities of β-amino acid ester derivatives containing a pyrimidine moiety was written by Bai, Song;Liu, Shan;Zhu, Yunying;Wei, Xian;Zhao, Kunhong;Li, Weihua;Wu, Qin. And the article was included in Heterocycles in 2018.Electric Literature of C7H11N3O2 This article mentions the following:

Both enantiomers of β-amino acid ester derivatives I (R¹ = cyclohexyl, Ph, 4-ClC₆H₄, 4-MeC₆H₄, 4-MeOC₆H₄, 2-furyl; R² = Me, Et) that contain a pyrimidine moiety were produced from 2-amino-4-(dimethoxymethyl)pyrimidine, aldehydes R¹CHO and malonates H₂C(CO₂R²)₂ in an enantioselective Mannich-type one-pot reaction in good yields and with excellent enantiomeric excess (up to >99% ee) using chiral cinchona alkaloid thiourea catalysts. An evaluation of the antiviral activities of reaction products against tobacco mosaic virus (TMV) was promising with high and selective biol. activities. Compound (-)-I (R¹ = 2-furyl; R² = Me) showed an excellent anti-TMV activity (curative activity, 56.1%; inactivation activity, 70.7%; protection activity, 95.7%) at 500 μg/mL. These values exceeded those of the com. available antiviral agent, ningnanmycin (curative activity, 52.6%; inactivation activity, 62.0%; protection activity, 90.2%). These novel chiral compounds were used as protective agents against TMV disease. In the experiment, the researchers used many compounds, for example, 4-Dimethoxymethylpyrimidin-2-ylamine (cas: 165807-05-6Electric Literature of C7H11N3O2).

4-Dimethoxymethylpyrimidin-2-ylamine (cas: 165807-05-6) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Drugs having the pyrimidine motif have manifested to exhibit gratifying biological activity like anticancer, antiviral, anti-inflammatory, antibacterial, and antihypertensive activities.Electric Literature of C7H11N3O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The tautomeric equilibria of thio analogs of nucleic acid bases. Part 1. 2-Thiouracil: background, preparation of model compounds, and gas-phase proton affinities was written by Katritzky, Alan R.;Baykut, Gokhan;Rachwal, Stanislaw;Szafran, Miroslaw;Caster, Kenneth C.;Eyler, John. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1989.Formula: C5H5ClN2O This article mentions the following:

The preparation is reported of all four of the monoalkyl derivatives of 2-thiouracil and of four of the six possible dialkyl derivatives required as models for a study of the tautomeric equilibrium by phys. methods. Gas-phase proton affinities are determined using ion cyclotron resonance mass spectrometry, and are used to provide quant. estimates of individual tautomer stabilities in the vapor state. These quant. results agree well with qual. deductions of predominant structures for the monoalkyl derivatives from IR spectroscopy. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-methoxypyrimidine (cas: 51421-99-9Formula: C5H5ClN2O).

4-Chloro-2-methoxypyrimidine (cas: 51421-99-9) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Formula: C5H5ClN2O

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Transformations of substituted 5-aminopyrimidines under conditions of diazotization was written by Nemeryuk, Michal P.;Sedov, Andrej L.;Safonova, Tamara S.;Cerny, Antonin;Krepelka, Jiri. And the article was included in Collection of Czechoslovak Chemical Communications in 1986.Computed Properties of C4H5N3O This article mentions the following:

Diazotization of aminopyrimidines I (R = H; R¹ = SMe, SCH₂Ph, OMe, H, OH; R² = OMe, Cl, OH, etc.) gave triazoles II (R³ = CO₂Me, COSMe, COSCH₂Ph, CONH₂, etc.). Under similar conditions diaminopyrimidines I [R = NH₂, R¹ = SCH₂C₆H₄R⁴-4 (R⁴ = NO₂, CO₂Et, CONHCHMe₂, H), R² = Me] gave pyrimidotriazine N-oxides III. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Computed Properties of C4H5N3O).

5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. 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.Computed Properties of C4H5N3O

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Studies on 5H-pyrimidothiazines. Part I. Synthesis of 6- and 7-carboxyalkyl derivatives of 5H-pyrimido[4,5-b][1,4]thiazine was written by Duro, F.;Santagati, N. A.;Scapini, G.. And the article was included in Farmaco, Edizione Scientifica in 1978.Formula: C4H5N3O This article mentions the following:

Primidothiazines I (R = H, R¹ = CO₂Me; R = Me, Ph, R¹ = CO₂Et; R = CO₂Et, R¹ = H) were obtained by treating 4-mercapto-5-aminopyrimidine (II) with HCOCHClCO₂Me, AcCHClCO₂Et, BzCHClCO₂Et, or BrCH₂COCO₂Et resp. I (R = CO₂Et, R¹ = H) was hydrolyzed to the acid. Reaction of I (R = Ph, R¹ = CO₂Et) with N₂H₄ gave the pyrazolone III, which was cleaved by N₂H₄ to II and 3-phenyl-3-pyrazoline-5-one. Reaction of II with BzCHClCO₂Et in the presence of NaOMe gave the ester IV, which was hydrolyzed to the acid and cyclized by HOAc to 5H-pyrimido[4,5-b][1,4]thiazin-6(7H)-one. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Formula: C4H5N3O).

5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Formula: C4H5N3O

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Gas- and liquid-phase C-H acidity of terminal acetylenes was written by Tupitsyn, I. F.;Popov, A. S.;Shibaev, A. Yu.. And the article was included in Zhurnal Obshchei Khimii in 1992.Safety of 2-Ethynylpyrimidine This article mentions the following:

Both corrected AM1 and MINDO/3 methods constituted acceptable approximations for calculation of proton affinity of ethynyde carbanions. Decrease in heat of deprotonation along the series H_nXCCH (X = 2nd period element C, N, O, F) testifies to the predominant role of electronegativity in C-H acidity; bond-length variations along this series, however, indicate repulsive interactions between the carbanion center and heteroatom. Carbanion stability increases (proton affinity decreases) upon 2nd- to 3rd row exchange, e.g., from H₃CCC^– to H₃SiCC^–; that this stabilization originates in dπ-conjugation is substantiated by decreasing Si-C bond length in the carbanion vs. acid. Heat of deprotonation decreases from HCCH to RCCH (R = aryl, N-containing heteroaryl) regardless of the degree of electron deficiency or electron excess in the ring. Correlations of heat of deprotonation with exptl. pK_a (thermodn. acidity) and k_D (kinetics of H-D exchange, as measure of kinetic acidity) were discussed. In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0Safety of 2-Ethynylpyrimidine).

2-Ethynylpyrimidine (cas: 37972-24-0) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Safety of 2-Ethynylpyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia