cas 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine

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Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
supporting information
p. 146 - 153
(2020/03/10)

5-fluoro-2, 4-pyrimidine diamine compound as well as preparation and application thereof
The invention discloses a 5-fluoro-2, 4-pyrimidine diamine compound with a structure as shown in a formula (I), a preparation method thereof and application of the 5-fluoro-2, 4-pyrimidine diamine compound in preparation of an anti-tumor drug, and the anti-tumor drug is a drug for treating liver cancer, lung cancer or leukemia. The compound as shown in the formula (I) provided by the invention hasgood anti-tumor activity, and provides a basis for screening of new drugs; the compound has a remarkable inhibition effect on a HepG-2 cell strain, an A549 cell strain and an HL-60 cell strain; moreover, the invention provides the preparation method of the formula (I), the preparation method is simple, and industrial production is facilitated.
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Paragraph 0083-0085

(2020/05/30)

Triazole-modified 5-fluoro -2,4- pyrimidine diamine compound and application thereof (by machine translation)
5 - The invention provides a triazole-modified. fluorine - 22224-pyrimidine diamine compound and application thereof, and the compound has a certain inhibition effect (I) on HepG - 2 cell strain, A549 cell strain, HL - 60 cell strain, K - 562 cell strain to provide foundation, for new drug screening and, The preparation method; of the compound, is simple (I) and beneficial to industrial. production. (by machine translation)
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Paragraph 0100-0102

(2020/06/02)

Preparation method of chloro-substituted polyhydroxy aza-aromatic ring compound (by machine translation)
The invention discloses a preparation method, namely BTC and SOCl, of a chloropolyhydroxyl aza heteroaromatic ring compound as a raw material with a polyhydroxy aza heteroaromatic ring compound as a raw material, and a preparation method thereof. 2 As the double chlorination reagent, a chloropolyhydroxyl aza-aromatic ring compound is produced by chlorination reaction with 4 - dimethylaminopyridine (DMAP) as a catalyst at room temperature to reflux temperature of the reaction, as a catalyst. BTC TC TC TC2 /DMDMAP chlorination system has high efficiency, high selectivity and chlorine substitution on a polyhydroxy nitrogen heterocyclic compound; the system can replace POCl3 , The production of phosphorus-containing wastewater is avoided. Using BTC as a chlorination reagent, the reaction by-product was HCl and CO. 2 . From the aspects of industrial wastewater treatment, environmental protection and the like, the advantages thereof are obvious; SOCl is distilled off after the reaction is ended. 2 The quantity is almost no loss, can be used repeatedly, and reduces the process cost. (by machine translation)
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Paragraph 0019; 0020; 0021-0024

(2019/10/01)

Method for preparing 2,4-dichloro-5-fluoropyrimidine through ultraviolet photocatalytic reaction
The invention relates to a method for preparing 2,4-dichloro-5-fluoropyrimidine through an ultraviolet photocatalytic reaction. The problem of environmental pollution caused by preparation and waste acid treatment of 2,4-dichloro-5-fluoropyrimidine can be effectively solved. The method comprises the steps that 2,4-dimethoxy-5-fluoropyrimidine is dissolved in a solvent the weight volume of which is10-20 times that of the 2,4-dimethoxy-5-fluoropyrimidine, wherein according to the weight volume, the unit of solids is gram, and the unit of liquid is milliliter; a catalyst sulfuryl chloride is added, and the addition amount of the catalyst sulfuryl chloride is 2-5% of the mass of the 2,4-dichloro-5-fluoropyrimidine; after ultraviolet light irradiation is conducted for 10 minutes, chlorine gasis introduced, the reaction temperature is 15-30 DEG C, and stirring while chlorine introduction is conducted for 12 hours; an equal volume of ice water is added, liquid separation is conducted, an organic phase is washed with an aqueous sodium carbonate solution with the mass concentration of 5%, and water washing, drying and concentration under reduced pressure are conducted to form the solid product 2,4-dichloro-5-fluoropyrimidine. The preparation method is simple, easy to operate, low in cost and free of waste residues, effectively prevents environmental pollution and has significant economic and social benefits.
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Paragraph 0009-0011

(2019/06/12)

5-fluoro-uracil immunoassay
Novel conjugates of 5-fluoro-uracil and novel 5-fluoro-uracil immunogens and monoclonal antibodies generated by these immunogens which are useful in immunoassays for the quantification and monitoring of 5-fluoro-uracil in biological fluids.
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Page/Page column 15; 16; 19

(2017/02/28)

Flucytosine preparation method applicable to industrial production
The invention discloses a flucytosine preparation method applicable to industrial production. The method comprises the following steps: performing chlorination on fluorouracil, performing ammonification, and performing hydrolysis, thereby obtaining flucytosine. To solve defects, the invention provides the flucytosine preparation method applicable to industrial production, and the method is small in process procedure, simple in operation, low in investment cost, relatively good in prospect and applicable to large-scale industrial production.
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Paragraph 0013

(2017/08/27)

Novel voriconazole intermediate and synthesis of voriconazole
The present invention relates to a method for preparing voriconazole represented by the following chemical formula 1, which comprises the steps of: 1) subjecting a compound represented by the following chemical formula 4 and a compound represented by the following chemical formula 5 to Reformatsky type coupling reaction to obtain a compound represented by the following chemical formula 3; 2) removing the substituents, thiol group and chloro group, from the compound of chemical formula 3 to obtain a racemate voriconazole represented by the following chemical formula 2; and 3) carrying out optical isolation of the racemate compound of chemical formula 2 by using an optically active acid. In chemical formulae 1-5, R represents a substituent selected from phenyl, pyridine, pyrimidine, thiazole, benzothiazole, benzoxazole, imidazole, 1-methylimidazole, C1-C4 alkyl or a combination thereof, wherein each substituent of the above substituents independently represents at least one selected from a halo, nitro and methoxy.
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Paragraph 0090-0093

(2016/11/07)

Pharmaceutical Process and Intermediates
The present disclosure provides for processes and intermediates in the large-scale manufacture of the compound of formula (I) or hydrates thereof.
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Paragraph 0145

(2015/07/02)

Pyrimidineamines as angiogenesis modulators
Pyrimidine derivatives, which are useful as VEGFR2 inhibitors are described herein. The described invention also includes methods of making such pyrimidine derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.
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Paragraph 0162; 0163

(2015/11/16)

2,4-Pyrimidinediamine Compounds and Their Uses
The present invention provides 2,4-pyrimidinediamine compounds that inhibit the IgE and/or IgG receptor signaling cascades that lead to the release of chemical mediators, intermediates and methods of synthesizing the compounds and methods of using the compounds in a variety of contexts, including in the treatment and prevention of diseases characterized by, caused by or associated with the release of chemical mediators via degranulation and other processes effected by activation of the IgE and/or IgG receptor signaling cascades.
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Paragraph 0312

(2015/11/10)

PYRIDIN-2(1H)-ONE DERIVATIVES AS JAK INHIBITORS
New pyridin-2(1H)-one derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).
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Page/Page column 82

(2013/03/26)

Pyridin-2(1h)-one derivatives as jak inhibitors
New pyridin-2(1H)-one derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).
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Paragraph 0153

(2013/03/26)

Novel 5-fluorouracil derivatives: Synthesis and cytotoxic activity of 2-butoxy-4-substituted 5-fluoropyrimidines
Twenty two new 5-fluorouracil (5-FU) derivatives, 2-butoxy-4-substituted 5-fluoropyrimidines, were synthesized and characterized by IR, 1H NMR, MS, HRMS. All compounds were preliminarily evaluated by MTT assay on human liver BEL-7402 cancer cell line in vitro. Ten compounds were selected to test their cytotoxic activity against A549, HL-60 and MCF-7 cancer cell lines in vitro. These compounds were more sensitive to BEL-7402 than other cell lines, particularly, cytotoxic activity of compounds 6b, 6d-f, 6p, 6s-u were in sub-micromolar scale. The highest cytotoxic potency against A549, HL-60 and MCF-7 was shown by 2-butoxy-4-chloro-5- fluoropyrimidine (5) with IC 50 values of 0.10, 1.66 and 0.59 μM, respectively. Compounds 6d and 6e were effective against MCF-7 with IC50 9.73 μM and HL-60 with IC50 8.83 μM, respectively.
Sun, Jian,Zhang, Shi-Jie,Li, Hai-Bo,Zhou, Wei,Hu, Wei-Xiao,Shan, Shang
p. 1349 - 1354
(2013/07/28)

Solvent-free or low-solvent large-scale preparation of chloropyrimidine and analogues
Chloropyrimidine or other N-containing aromatic heterocyclic analogues can be efficiently prepared from the corresponding hydroxylated precursors under solvent-free or low-solvent conditions with equimolar or less chlorinating reagents. This high-yielding protocol allows successful preparations of multigram and kilogram batches of these important synthetic intermediates.
Sun, Zhihua,Wang, Han,Wen, Kun,Li, Ya,Fan, Erkang
experimental part
p. 4149 - 4153
(2011/07/07)

IMIDAZOPYRIDINE DERIVATIVES AS JAK INHIBITORS
New imidazopyridine derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).
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Page/Page column 112

(2011/07/09)

Imidazopyridine derivatives as JAK inhibitors
New imidazopyridine derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).
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Paragraph 0144; 0145

(2013/03/26)

Design and synthesis of pyrimidinone and pyrimidinedione inhibitors of dipeptidyl peptidase IV
The discovery of two classes of heterocyclic dipeptidyl peptidase IV (DPP-4) inhibitors, pyrimidinones and pyrimidinediones, is described. After a single oral dose, these potent, selective, and noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and lowering of blood glucose in animal models of diabetes. Compounds 13a, 27b, and 27j were selected for development.
Zhang, Zhiyuan,Wallace, Michael B.,Feng, Jun,Stafford, Jeffrey A.,Skene, Robert J.,Shi, Lihong,Lee, Bumsup,Aertgeerts, Kathleen,Jennings, Andy,Xu, Rongda,Kassel, Daniel B.,Kaldor, Stephen W.,Navre, Marc,Webb, David R.,Gwaltney, Stephen L.
scheme or table
p. 510 - 524
(2011/03/20)

Theramutein modulators
This invention relates to agents that are inhibitors or activators of variant forms of endogenous proteins and novel methods of identifying such variants. Of particular interest are inhibitors and activators of endogenous protein variants, encoded by genes which have mutated, which variants often arise or are at least first identified as having arisen following exposure to a chemical agent which is known to be an inhibitor or activator of the corresponding unmutated endogenous protein.
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Page/Page column 168

(2010/02/17)

Process for the identification of novel enzyme interacting compounds
The present invention relates to methods for the characterization of enzymes or of enzyme-compound complexes, wherein the enzyme is obtained from a protein preparation with the help of at least one broad spectrum ligand immobilized on a solid support and wherein the enzyme is characterized by mass spectrometry. These methods are useful for the screening of non-immobilized compound libraries, selectivity profiling of lead compounds and mechanism of action studies in living cells.
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(2009/10/01)

THERAMUTEIN MODULATORS
This invention relates to agents that are inhibitors or activators of variant forms of endogenous proteins and novel methods of identifying such variants. Of particular interest are inhibitors and activators of endogenous protein variants, encoded by genes which have mutated, which variants often arise or are at least first identified as having arisen following exposure to a chemical agent which is known to be an inhibitor or activator of the corresponding unmutated endogenous protein.
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Page/Page column 199; 235

(2008/12/07)

POLYMORPHS OF TARTRATE SALT OF 2-[2-(3-(R)-AMINO-PIPERIDIN-1-YL)-5-FLUORO-6-OXO-6H-PYRIMIDIN-1-YLMETHYL]-BENZONITRILE AND METHODS OF USE THEREFOR
Compositions comprising Compound I, wherein the Compound I is present in one or more polymorphic forms. Also provided are kits and articles of manufacture with compositions comprising one or more polymorphs of Compound I, and methods of using the compositions to treat various diseases.
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Page/Page column 19; 20

(2010/11/26)

Synthesis of 2,4-pyrimidinediamine compounds
The present invention provides an economical and efficient method to prepare various substituted 2,4-pyrimidinediamine compounds in large scale quantities.
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Page/Page column 17-18

(2008/06/13)

Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders
Aryl sulfonamide and sulfonyl compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.
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Page/Page column 64

(2010/02/14)

Dipeptidyl peptidase inhibitors
Compounds, pharmaceuticals, kits and methods are provided for use with DPP-IV inhibitors comprising Formula I: wherein the substituents are as described herein.
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Page/Page column 67

(2008/06/13)

Preparation of triazoles by organometallic addition to ketones and intermediates therefor
A process for the preparation of a compound of the formula: or an acid addition or base salt thereof, wherein R is phenyl optionally substituted by 1 to 3 substituents each independently selected from halo and trifluoromethyl; R1 is C1-C6 alkyl; and “Het” is pyrimidinyl optionally substituted by 1 to 3 substituents each independently selected from C1-C4 alkyl, C1-C4 alkoxy, halo, oxo, benzyl and benzyloxy, comprising reacting a compound of the formula: with a compound of the formula wherein X is chloro, bromo or iodo, the reaction taking place in the presence of zinc; at least one of iodine or a Lewis acid; and an aprotic organic solvent: optionally further reacting the resulting compound with an acid or base to form the corresponding acid addition or base salt thereof.
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(2008/06/13)

Cyclin-dependent kinase 4 inhibitors as a treatment for cancer. Part 2: Identification and optimisation of substituted 2,4-bis anilino pyrimidines
Through chemical modification and X-ray crystallography we identified the 2,4-bis anilino pyrimidines as potent inhibitors of CDK4. Herein, we describe the optimisation of this series.
Breault, Gloria A.,Ellston, Rebecca P. A.,Green, Stephen,James, S. Russell,Jewsbury, Philip J.,Midgley, Catherine J.,Pauptit, Richard A.,Minshull, Claire A.,Tucker, Julie A.,Pease, J. Elizabeth
p. 2961 - 2966
(2007/10/03)

N-substituted nonaryl-heterocyclic NMDA/NR2B antagonists
Compounds represented by Formula (I): 1or pharmaceutically acceptable salts thereof, are effective as NMDA NR2B antagonists useful for relieving pain.
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(2019/08/08)

Process development of voriconazole: A novel broad-spectrum triazole antifungal agent
In the synthesis of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1- yl)-2-butanol (voriconazole), the relative stereochemistry is set in the addition of a 4-(1-metalloethyl)-5-fluoropyrimidine derivative to 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone. The diastereo-control of this reaction has been examined by variation of pyrimidine substitution pattern and by changes in the metalation and reaction conditions. Excellent diastereoselection (12: 1) is obtained using an organozinc derivative of 6-(1-bromoethyl)-4-chloro-5-fluoropyrimidine. After removal of the chlorine from the pyrimidine ring, the absolute stereochemistry of voriconazole is established via a diastereomeric salt resolution process using (1R)-10-camphorsulfonic acid. Synthetic routes to the pyrimidine partner have also been evaluated. The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of methyl 3-oxopentanoate and cyclisation with formamidine acetate.
Butters, Mike,Ebbs, Julie,Green, Stuart P.,MacRae, Julie,Morland, Matthew C.,Murtiashaw, Charles W.,Pettman, Alan J.
p. 28 - 36
(2013/09/07)

Synthesis, conformation and biological properties of selenonucleosides
Synthesis, conformation and antitumour properties of novel 2- and 4- selenopyrimidine nucleosides are described.
Felczak, Krzysztof,Miazga, Agnieszka,Golos, Barbara,Rode, Wojciech,Shugar, David,Kulikowski, Tadeusz
p. 635 - 636
(2007/10/03)

Pyridonecarboxylic acid derivatives or their salts and antibacterial agent comprising the same as the active ingredient
A pyridonecarboxylic acid derivative represented by the following general formula (1): STR1 [wherein R1 represents hydrogen atom or a carboxyl protective group; R2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R3 represents hydrogen atom or a halogen atom; R4 represents hydrogen atom or a halogen atom; R5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH= or --CR7 = (wherein R7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represent the nitrogen atom), and W represents nitrogen atom or --CR8 = (wherein R8 represents hydrogen atom, a halogen atom, or a lower alkyl group)] or its salt, as well as an antibacterial agent containing such compound are provided.
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(2008/06/13)

Stereocontrolled synthesis of β-2'-deoxypyrimidine nucleosides via intramolecular glycosylations
A pyrimidine moiety was tethered at the 3'-β-position of D-threo-furanosides. By carefully controlling the reaction conditions, pyrimidine bases can be delivered to the anomeric center to give of β-pyrimidine nucleosides in good yield and with complete stereocontrol.
Xia, Xiaoyang,Wang, Jianying,Hager, Michael W.,Sisti, Nicholas,Liotta, Dennis C.
p. 1111 - 1114
(2007/10/03)

Triazole antifungal agents
The invention provide antifungal compounds of the formula: STR1 and pharmaceutically acceptable salts thereof, wherein R is phenyl substituted by 1 to 3 substituents each independently selected from halo, --CF3 and --OCF3 ; R1 is C1 -C4 alkyl; R2 is H or C1 -C4 alkyl; X is CH or N; and Y is F or Cl.
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(2008/06/13)

SYNTHESIS AND AMINATION OF 2,4-DICHLORO-5-FLUOROPYRIMIDINE
2,4-Dichloro-5-fluoropyrimidine was prepared by the chlorination of 5-fluorouracil with phosphorus pentachloride in absence of solvent.The reaction of 2,4-dichloro-5-pyrimidine with primary and secondary aliphatic and heteroaromatic amines in an aqueous medium yields 2-chloro-4-RR'-amino-5-fluoropyrimidines, with stereoselective substitution of chlorine in the C4 position.The substances obtained have well-defined fungicidal activity.
Kovalenko, A. L.,Krutikov, V. I.,Zolotukhina, M. M.,Alekseeva, L. E.
p. 1122 - 1125
(2007/10/02)

Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-b icyclo[2.2.1]heptanedicarboxime (Tandospirone) and related compounds
A series of cyclic imides bearing a ω-(4-aryl and 4-heteroaryl-1-piperazinyl)alkyl moieties was synthesized and tested in vivo for anxiolytic activity. The in vitro binding affinities of these compounds were also examined for 5-HT(1A) receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3- bicyclo[2.2.1]heptanedicarboximide (1: tandospirone), was found to be equipotent with buspirone in its anxiolytic activity and more anxio-selective than buspirone and diazepam. Tandospirone (1) is currently undergoing clinical evaluation as a selective anxiolytic agent.
Ishizumi,Kojima,Antoku
p. 2288 - 2300
(2007/10/02)

A NEW ROUTE TO THE SYNTHESIS OF 5-FLUOROURACIL
Starting from tetrafluoropyrimidine (1), selective fluorine/chlorine exchange reactions and selective hydrogenolysis of the chlorine substituents are described.Combination of these methods, together with a subsequent hydrolysis reaction, provides a new route to the synthesis of 5-fluorouracil via 4,6-dichloro-2,5-difluoropyrimidine and 4-chloro-2,5-difluoropyrimidine.
Baasner, B.,Klauke, E.
p. 417 - 430
(2007/10/02)