- Preparation method 2 - methyl -5 -bromopyrimidine
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The invention specifically discloses a preparation method of 2 - methyl -5 -bromopyrimidine, and belongs to the technical field of organic synthesis. The method comprises the following steps: a) taking 2 - amino -5 -bromopyrimidine as a raw material, carrying out diazotization reaction or Schedman reaction or 2 - hydroxyl -5 -bromopyrimidine as a raw material to obtain 2 -halo -5 -bromopyrimidine through a halogenated reagent. b) The carboxylic diester is substituted with 2 - halo -5 - bromopyrimidine to give 2-position substituted product. c) The last 2 -bit substituted product is reacted under basic, high temperature conditions to give 2 - methyl -5 - bromopyrimidine. The method has the advantages of easily available raw materials, low cost, simple flow and potential industrial amplification prospect.
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Paragraph 0034-0036
(2021/11/26)
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- Dimethyl sulfoxide-accelerated reductive deamination of aromatic amines with t-BuONO in tetrahydrofuran
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An efficient method for the conversion of aryl amines into arenes by a one-pot reductive deamination has been achieved. It was found the reductive deamination using t-BuONO in tetrahydrofuran could be accelerated by dimethyl sulfoxide and provided the deamination products with good yields under mild conditions. A plausible mechanism is discussed.
- Fang, Lu,Qi, Liang,Ye, Longfei,Pan, Zhentao,Luo, Wenjun,Ling, Fei,Zhong, Weihui
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p. 579 - 583
(2018/11/27)
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- Preparation method for 2-chloro-5-(piperidin-4-yl)pyrimidine
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The invention discloses a preparation method for 2-chloro-5-(piperidin-4-yl)pyrimidine. The target product is obtained by using 2-chloropyrimidine as a starting raw material, performing a brominationreaction, performing a coupling reaction, performing an elimination reaction and performing a catalytic hydrogenation reaction. The compound provided by the invention is an important pharmaceutical intermediate.
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Paragraph 0020; 0021; 0022
(2018/04/02)
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- Method for preparing 2-chloropyrimidine derivative
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The invention discloses a method for preparing a 2-chloropyrimidine derivative, namely 2-chlorine-5-(piperidine-4-yl) pyrimidine. The method comprises the following steps: by taking 2-chloropyrimidine as an initial raw material, performing reactions of bromine introduction, coupling, elimination and catalytic hydrogenation, thereby obtaining a target product. The compound is a significant medicinal intermediate.
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Paragraph 0021; 0022
(2017/12/27)
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- Preparation of 2-amino-pyrimidine-5-boronic acid frequency that ester method
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A method of preparing 2-aminopyrimidine-5-boronic acid pinacol ester is disclosed. The method includes subjecting 2-chloropyrimidine that is a raw material and NBS to bromization under catalysis of BF3-Et2O to obtain 2-chloro-5-bromopyrimidine; reacting the 2-chloro-5-bromopyrimidine with n-Bu3MgLi at a temperature ranging from -20 DEG C to -10 DEG C; adding methoxyboronic acid pinacol ester or isopropoxyboronic acid pinacol ester; performing boronization to obtain 2-chloropyrimidine-5-boronic acid pinacol ester; adding into ammonia water or a methanol-ammonia solution; and reacting at 80-100 DEG C in a sealed manner to obtain the 2-chloropyrimidine-5-boronic acid pinacol ester. Synthetic process conditions of the method are mild. An ultralow-temperature reaction is avoided. Reactions can be performed continuously. A pure product can be obtained only by simple recrystallization of the final product.
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Paragraph 0017
(2017/01/02)
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- Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents
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The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.
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Page/Page column 289
(2015/11/16)
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- SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY
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The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
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Page/Page column 111
(2015/01/07)
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- OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY
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The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
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Page/Page column 105
(2015/01/07)
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- Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety
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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
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p. 467 - 474
(2012/11/07)
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- Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities
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The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.
- Sun, Xicheng,Qiu, Jian,Strong, Sarah A.,Green, Louis S.,Wasley, Jan W.F.,Blonder, Joan P.,Colagiovanni, Dorothy B.,Mutka, Sarah C.,Stout, Adam M.,Richards, Jane P.,Rosenthal, Gary J.
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supporting information; experimental part
p. 5849 - 5853
(2011/10/19)
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- 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
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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)
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- A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants
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(Chemical Equation Presented) A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.
- Nara, Susheel J.,Jha, Mukund,Brinkhorst, Johan,Zemanek, Tony J.,Pratt, Derek A.
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supporting information; experimental part
p. 9326 - 9333
(2009/04/06)
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- Simple microwave-assisted ligand-free Suzuki cross-coupling: Functionalization of halo-pyrimidine moieties
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(Chemical Equation Presented) An advantageous ligand-free protocol for Suzuki couplings is described. The synthetic procedure entails microwave irradiation for the reduction of the reaction times and the use of silica cartridges for the purification. Dihalo-pyrimidine structures, interesting scaffolds in medicinal chemistry, were chosen as test compounds.
- Colombo, Matteo,Giglio, Marco,Peretto, Ilaria
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p. 1077 - 1081
(2008/12/20)
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- Development of a concise scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine via a Negishi cross-coupling
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A practical and scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine, an intermediate in the synthesis of a selective PDE-V inhibitor, was developed. A Negishi cross-coupling between the in situ prepared 2-pyridylzinc chloride and 5-iodo-2-chloropyrimidine catalyzed by Pd(PPh3)4 afforded the product in one step. Development of a convenient purification did away with the necessity of chromatography, allowing the preparation of the product on kilogram scale.
- Perez-Balado, Carlos,Willemsens, Albert,Ormerod, Dominic,Aelterman, Wim,Mertens, Narda
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p. 237 - 240
(2012/12/26)
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- Novel diazine derivatives
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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)
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- PYRIMIDINE-SULFAMIDES AND THEIR USE AS ENDOTHELIAN RECEPTOR ANTAGONIST
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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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- 2,5-substituted pyrimidine derivatives-CCR-3 receptor antagonists
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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)
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- Improved synthesis of 2,2′-bipyrimidine
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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.
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p. 6550 - 6552
(2007/10/03)
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- The synthesis and characterisation of novel thienyl-pyrimidine liquid crystalline materials
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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
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p. 279 - 292
(2007/10/03)
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- Practically perfect asymmetric autocatalysis with (2-alkynyl-5- pyrimidyl)alkanols
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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
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p. 659 - 661
(2007/10/03)
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- 5-Bromo-2-iodopyrimidine: A novel, useful intermediate in selective palladium-catalysed cross-coupling reactions for efficient convergent syntheses
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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.
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p. 2719 - 2720
(2007/10/03)
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