cas 38353-06-9, 5-Bromo-2-hydroxypyrimidine

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Rates and equilibrium constants for the covalent hydration of 5-bromo-2(1H)-pyrimidinone in aqueous solution
The kinetics of bromination of the title compound (1) have been measured in aqueous solutions of pH 0-6.The change in the order of reaction which occurs around pH 2.5 is explained by 1 reacting via its covalent hydrate, 3.Furthermore, there is sufficient 3 present at equilibrium that the kinetics of its equilibration with 1 were also measured.From these two studies the extent of covalent hydration of 1 is estimated to be 5percent.Kinetic studies of the bromination of the dimethyl cation 5 and of its equilibration with the pseudobase 6 were also carried out for the purposes of comparison.The present results for 1, 3, 5 and 6 are compared to earlier results for 2-pyrimidinone and analogous derivatives.
Tee, Oswald S.,Pika, Jana,Kornblatt, Judith M.,Trani, Michael
p. 1267 - 1272
(1986)
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One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry
Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.
Braje, Wilfried,Geneste, Hervé,Rodrigo, Eduardo,Walter, Magnus W.,Wiechert, Rainer
supporting information
p. 1469 - 1473
(2022/03/07)

Characterization of degradation products of macitentan under various stress conditions using liquid chromatography/mass spectrometry
Rationale: Stress testing of a drug candidate is an important step in the drug discovery and development process. The presence of degradation products in a drug affects the quality as well as the safety and efficacy of drug formulation. Hence, it is essential to develop an efficient analytical method which could be useful for the separation, identification and characterization of all possible degradation products (DPs) of a drug. Macitentan (MT) is an endothelin receptor antagonist (ERA) drug used to treat high blood pressure in the lungs. Comprehensive stress testing of MT was carried out as per ICH guidelines to understand the degradation profile of the drug. Methods: MT was subjected to various stress conditions such as acidic, basic, neutral hydrolysis, oxidation, photolysis and thermal conditions; and the resulting degradation products were investigated using liquid chromatography/diode-array detection/electrospray ionization high-resolution mass spectrometry (LC/DAD/ESI-HRMS) and tandem mass spectrometry (MS/MS) techniques. An efficient and simple ultra-high-performance liquid chromatography (UHPLC) method has been developed using an Accucore C18 column (4.6?×?150?mm, 2.6?μm) using a gradient elution of 5?mM ammonium formate and acetonitrile as mobile phases. Results: MT was found to degrade under acid and base hydrolysis stress conditions; whereas it was stable under oxidation, neutral hydrolysis, thermal and photolytic conditions. MT formed nine DPs (DP1 to DP9) and one DP (DP10) under acidic and basic hydrolytic conditions, respectively. All the degradation products (DP1 to DP10) were identified and characterized by LC/MS/MS in positive ion mode with accurate mass measurements. Conclusions: MT was found to be labile under hydrolytic conditions. The structures of the DPs were characterized by appropriate mechanisms. The proposed method can be effectively used for the characterization of MT and its DPs.
Yerra, Naga Veera,Pallerla, Pavankumar,Pandeti, Sukanya,Tabet, Jean-Claude,Thota, Jagadeshwar Reddy
p. 1075 - 1084
(2018/06/11)

FACTOR IXA INHIBITORS
In its many embodiments, the present invention provides a novel class of benzamide compounds represented by Formula (I) or pharmaceutically acceptable salts or solvates thereof, or pharmaceutical compositions comprising one or more said compounds or pharmaceutically acceptable salts or solvates thereof, and methods for using said compounds or pharmaceutically acceptable salts or solvates thereof for treating or preventing a thromboses, embolisms, hypercoagulability or fibrotic changes.
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Page/Page column 155

(2015/11/09)

FACTOR IXA INHIBITORS
In its many embodiments, the present invention provides a novel class of benzamide compounds represented by Formula (I) or pharmaceutically acceptable salts or solvates thereof, or pharmaceutical compositions comprising one or more said compounds or pharmaceutically acceptable salts or solvates thereof, and methods for using said compounds or pharmaceutically acceptable salts or solvates thereof for treating or preventing a thromboses, embolisms, hypercoagulability or fibrotic changes.
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Page/Page column 142

(2015/11/09)

Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety
A series of 5-bromo-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine were prepared under conventional heating as well as microwave reaction condition. The newly synthesized compounds were characterized on the basis of elemental, spectral and single crystal X-ray studies. These new compounds were screened for their antioxidant, anti-inflammatory and analgesic activities. Some of these compounds exhibited potent biological activities compared to the standard drug.
Adhikari, Adithya,Kalluraya, Balakrishna,Sujith, Kizhakke Veedu,Gouthamchandra, Kuluvar,Jairam, Ravikumar,Mahmood, Riaz,Sankolli, Ravish
p. 467 - 474
(2012/11/07)

INHIBITORS OF ACETYL-COA CARBOXYLASE
The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 64-65

(2010/11/17)

2-ALKYNYL-6-PYRIDIN-2-YL-PYRIDAZINONES, 2-ALKYNYL-6-PYRIDIN-2-YL-DIHYDROPYRIDAZINONES, 2-ALKYNYL-6-PYRIMIDIN-2-YL-PYRIDAZINONES AND 2-ALKYNYL-6-PYRIMIDIN-2-YL-DIHYDROPYRIDAZINONES AND THEIR USE AS FUNGICIDES
This invention relates to certain novel 2-alkynyl-6-pyridin-2-yl-pyridazinones, 2-alkynyl-6-pyridin-2-yl-dihydropyridazinones, 2-alkynyl-6-pyrimidin-2-yl-pyridazinones and 2-alkynyl-6-pyrimidin-2-yl-dihydropyridazinones and to the use of these compounds for control of fungal pathogens of plants and mammals.
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Page/Page column 15

(2009/10/17)

Novel diazine derivatives
The present invention provides compounds of formula (I): their pharmaceutically acceptable salts or esters, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, pharmaceutical compositions containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.
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Page/Page column 15

(2010/02/14)

INDOLES USEFUL IN THE TREATMENT OF INFLAMMATION
There is provided a compound of formula: (I), wherein X, R1, R2, R3, R4, R5 and R6 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of microsomal prostaglandin E synthase-1 is desired and/or required, and particularly in the treatment of inflammation.
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Page/Page column 84

(2010/02/15)

PYRIMIDINE-SULFAMIDES AND THEIR USE AS ENDOTHELIAN RECEPTOR ANTAGONIST
The invention relates to novel sulfamic acid amides of General Formula (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists. [ADD FORMULA]
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Page 22

(2008/06/13)

2,5-substituted pyrimidine derivatives-CCR-3 receptor antagonists
This invention relates to certain pyrimidine derivatives that are CCR-3 receptor antagonists, pharmaceutical compositions containing them, methods for their use and methods for preparing these compounds.
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Page/Page column 24; 30-31

(2010/02/05)

Improved synthesis of 2,2′-bipyrimidine
A high-yield synthesis was developed for the preparation of 2,2′-bipyrimidine (1) using the Ullmann coupling of 2-iodopyrimidine. The new procedure was also used for the preparation of 4,4′,6,6′-tetramethyl-2,2′-bipyrimidine (2) and 5,5′-dibromo-2,2′-bipyrimidine (3).
Vlad, Gabor,Horvath, Istvan T.
p. 6550 - 6552
(2007/10/03)

The synthesis and characterisation of novel thienyl-pyrimidine liquid crystalline materials
The synthesis and transition temperatures of a series of novel thienyl-pyrimidine liquid crystalline materials is described. Palladium catalysed coupling of 5-n-alkyl-2-tri-n-butylstannyl thiophenes to 5-bromo-2-iodopyrimidine is used to create novel pyrimidine compounds which exhibit lower melting points than similar pyrimidine liquid crystals. These compounds exhibit a variety of phases including smectic A, C, G, B and hexstatic B also they exhibit several as yet unidentifiable phases. Speculation as to hydrogen bonding in the liquid crystalline core is also discussed therein.
Wilson, Paul,Lacey, David,Sharma, Sanjay,Worthington, Brenda
p. 279 - 292
(2007/10/03)

Pyrrolidine derivatives-CCR-3 receptor antagonists
This invention relates to certain 3-aminomethylpyrrolidine derivatives of Formula (I): that are CCR-3 receptor antagonists, pharmaceutical compositions containing them, methods for their use and methods for preparing these compounds.
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(2008/06/13)

Practically perfect asymmetric autocatalysis with (2-alkynyl-5- pyrimidyl)alkanols
Extremely high enantioselectivity (> 99.5% ee) and chemical yield (> 99%) are achieved in an asymmetric autocatalytic reaction. A (5- pyrimidyl)alkanol with a tert-butylethynyl group at its 2-position (1) is a very efficient asymmetric autocatalyst in the enantioselective alkylation in Equation (1).
Shibata,Yonekubo,Soai
p. 659 - 661
(2007/10/03)

Matrix-isolation FT-IR studies and ab initio calculations of hydrogen-bonded complexes of molecules modeling cytosine or isocytosine tautomers. 6. Experimental observation of a water-induced tautomeric shift for 2-hydroxypyrimidine and 5-bromo-2-hydroxypyrimidine
The H-bond interaction of the cytosine model compound 2-hydroxypyrimidine and its 5-bromo derivative with water is investigated using the combined matrix-isolation FT-IR and theoretical ab initio method. As predicted by the ab initio calculations, both compounds occur dominantly in the hydroxy tautomeric forms. The estimated KT(h/o) values are 60 and 184, respectively. When water is added to the Ar matrix, a noticeable shift of the tautomeric equilibrium towards the oxo form is observed. The theoretical results indicate that the closed N...H-O(H)...H-O and C=O...H-O(H)...H-N H-bonded water complexes are the most stable systems for the hydroxy and the oxo tautomers, respectively. The experimental spectra are consistent with this prediction, but additional structures, such as an open N...H-OH complex of the hydroxy tautomer, are also identified. The frequency shift of the stretching mode of doubly H-bonded water in the two closed complexes is larger, and the ratio between the calculated and measured frequencies smaller than expected from the correlation established before for open, singly H-bonded complexes involving similar molecules. Although some cooperativity exists between the two H bonds in each of the closed complexes, this effect is limited because the geometrical structures of both H bonds are noticeably perturbed from the perfect alignment due to the cyclic arrangement of the complex. A possible mechanism of the proton transfer process leading from the hydroxy to the oxo tautomeric form is discussed in terms of proton tunneling and in relation to recent literature data.
Smets, Johan,Destexhe, Alain,Adamowicz, Ludwik,Maes, Guido
p. 8157 - 8168
(2007/10/03)

5-Bromo-2-iodopyrimidine: A novel, useful intermediate in selective palladium-catalysed cross-coupling reactions for efficient convergent syntheses
A simple synthesis of the novel 5-bromo-2-iodopyrimidine is described and examples are provided of the use of the compound in selective palladium-catalysed cross-coupling reactions with a wide range of arylboronic acids and alkynylzincs to give the efficient syntheses of many substituted pyrimidine compounds.
Goodby, John W.,Hird, Michael,Lewis, Robert A.,Toyne, Kenneth J.
p. 2719 - 2720
(2007/10/03)

Naphthyl organic compounds
Liquid crystal compounds of formula (I) are described, where formula (I) is given as R1 --A--(Xm --(B)n --R2 where A is selected from nathyl, flourinated naphthyl, brominated naphthyl, B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C C, COO and C C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine. Also described are liquid crystal compounds suitable for inclusion in devices utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase and described by formula (II): R3 --J--(Y)p --(Z)q --R 4, where J is selected from nathyl, fluorinated naphthyl, brominated naphthyl, Z is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, Y is selected from C=C, COO and C=C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0.
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(2008/06/13)

Syntheses of 5-Alkenylpyrimidines by Organotin Reactions
5-Stannylpyrimidines can be prepared from the corresponding bromides by lithiation at -95 deg C and quenching with tributylstannyl chloride.The 5-stannyl-pyrimidine is used in Pd-catalyzed coupling reactions with vinyl bromides.The opposite reaction sequence, i.e.Pd-catalyzed coupling between 5-halopyrimidines and vinyltin derivatives, is also described.Alternatively, the 5-vinylpyrimidines have been obtained by dehydrohalogenation with cesium fluoride and by a modified Wittig reaction. 2-Methylthiopyrimidines are transformed into the 2-methoxy derivatives or 2-pyrimidinones using chloramine-T (CAT) in a simple one-pot synthesis.
Sandosham, Jessie,Benneche, Tore,Moeller, Bjoerg,Undheim, Kjell
p. 455 - 461
(2007/10/02)

Synthesis and Biological Activities of 2-Pyrimidinone Nucleosides. 2. 5-Halo-2-pyrimidinone 2'-Deoxyribonucleosides
1-(2-Deoxy-β-D-ribofuranosyl)-5-bromo-2-pyrimidinone (BrPdR) and 1-(2-deoxy-β-D-ribofuranosyl)-5-iodo-2-pyrimidinone (IPdR) have been synthesized by condensation of the appropriate silylated bases 2a and 2b, respectively, with 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (8) in 1,2-dichloroethane, in the presence of SnCl4, followed by separation of the anomeric blocked nucleosides via column chromatography and subsequent deprotection with methanolic ammonia.Both BrPdR and IPdR exhibited significant antiherpes activities against various strains of HSV-1 and HSV-2, the latter compound (IPdR) showing the higher activity as well as the stronger binding to the virus-specific thimidine kinase.
Efange, Simon M. N.,Alessi, Elaine M.,Shih, H. C.,Cheng, Yung-Chi,Bardos, Thomas J.
p. 904 - 910
(2007/10/02)

O,O-dialkyl-5-halo-pyrimidin(2) yl-thionophosphoric acid esters
O,O-Dialkyl-5-halo-pyrimidin(2)yl-thionophosphoric acid esters of the formula STR1 in which R is methyl or ethyl and R' is halogen, Which possess insecticidal and acaricidal properties.
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(2008/06/13)

O-Alkyl-O-pyrimidin (2)yl-thionophosphonic acid esters
O-Alkyl-O-pyrimidin(2)yl-thionophosphonic acid esters of the formula STR1 in which R is alkyl with 1 to 6 carbon atoms, R' is alkyl with 1 to 6 carbon atoms or phenyl, R" and RIV each independently is hydrogen or alkyl with 1 to 4 carbon atoms, and R'" is halogen or hydrogen. Which possess insecticidal, acaricidal and nematocidal properties.
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(2008/06/13)