- Synthesis method 2 -fluoro -5 -trifluoromethyl pyrimidine
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The invention relates to the technical field of drug synthesis, and provides a synthesis method of 2 -fluoro -5 -trifluoromethyl pyrimidine. 5 - Methyluracil is used as a raw material and is subjected to cyclic chlorination reaction. Redox reaction, chlorination reaction and fluorination reaction obtain the target product, the process is simple, the raw materials are cheap and easily available, the yield is high, and no heavy metal pollution is generated in the whole process. In the chlorination reaction, phosphorus oxychloride is used for chlorination, chlorine is used for chlorination in the chlorination reaction, the cost of the chlorination reaction is low, phosphorus pentachloride is used for recycling phosphorus oxychloride in the cyclochlorination reaction, and the reaction cost can be further reduced.
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Paragraph 0039; 0056-0057
(2021/10/20)
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- Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
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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
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supporting information
p. 146 - 153
(2020/03/10)
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- Preparation method of chloro-substituted polyhydroxy aza-aromatic ring compound (by machine translation)
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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)
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- COMPOUNDS FOR TREATING TUBERCULOSIS
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The present invention relates to pyrimidine compounds and compositions for treating tuberculosis. These compounds may be used to target the F1 domain of F-ATP synthase and may be used with bedaquiline or 6-chloro-2-ethyl-N-[[4-[4- [4-(trifluoromethoxy)phenyl]piperidin-1 -yl]phenyl]methyl]imidazo[1,2-a]pyridine-3-carboxamide (Q203) or a combination thereof.
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Paragraph 0099
(2018/09/18)
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- Large-scale solvent-free chlorination of hydroxy-pyrimidines,-pyridines,- pyrazines and-amides using equimolar POCl3
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Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines,-quinoxalines, or even-amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.
- Wang, Han,Wen, Kun,Wang, Le,Xiang, Ye,Xu, Xiaocheng,Shen, Yongjia,Sun, Zhihua
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experimental part
p. 4533 - 4544
(2012/06/30)
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- 2,4-DIAMINOPYRIMIDINE DERIVATIVES USEFUL AS INHIBITORS OF AURORA KINASE
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A 2,4-diaminopyrimidine derivative of the formula (I), or a pharmaceutically acceptable salt thereof, formula (I) wherein R1, R2, R3, R4, X and Y are as defined in the specification; together with processes for their preparation; pharmaceutical compositions containing them; and their use in therapy. The compounds are inhibitors of Aurora kinase.
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Page/Page column 44
(2009/06/27)
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- New compounds
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The present invention encompasses compounds of general formula (1) wherein R1, R2, R4, X, m, n and p are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.
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Page/Page column 16
(2009/07/10)
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- Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders
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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 63
(2010/02/14)
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- Cyclin-dependent kinase 4 inhibitors as a treatment for cancer. Part 2: Identification and optimisation of substituted 2,4-bis anilino pyrimidines
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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
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p. 2961 - 2966
(2007/10/03)
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- Synthesis, molecular modeling and biological activity of methyl and thiomethyl substituted pyrimidines as corticotropin releasing hormone type 1 antagonists
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Four small, targeted libraries of differentially substituted amino pyrimidines were synthesized in moderate to good yields. Excellent regiochemistry was observed for substitution at C2/C4 with selectivity >50 : 1 noted. All analogues were screened for their ability to interact with CRH 1 and CRH2 receptors. In all instances only poor agonistic and/or antagonistic behaviour was noted at CRH2. However, several compounds were potent and selective CRH1 antagonists, most notably 13a K1 = 39 nM. Additionally we have utilized these data and that recently reported by others to refine our original CRH1 pharmacophore (J. Med. Chem., 1999, 42, 2351-2357).
- McCluskey, Adam,Keller, Paul A.,Morgan, Jody,Garner, James
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p. 3353 - 3361
(2007/10/03)
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- Stereocontrolled synthesis of β-2'-deoxypyrimidine nucleosides via intramolecular glycosylations
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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.
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p. 1111 - 1114
(2007/10/03)
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- A new synthesis of 5-trifluoromethyluracil
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5-Trifluoromethyluracil, an important intermediate for the preparation of the antiviral trifluridine, is obtained by chlorinating thymine to give the new 2,4-dichloro-5-trichloromethylpyrimidine. Reacting the latter with hydrogen fluoride yields the new 2,4-difluoro-5-trifluoromethylpyrimidine, and hydrolysis with water gives 5-trifluoromethyluracil in high purity and good yield.
- Andres, Peter,Marhold, Albrecht
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- Process for the preparation of chloropyrimidines
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A process for the preparation of chloropyrimidines of the formula STR1 in which the substituents may be alkyl, cycloalkyl, aryl or radicals containing heteroatoms, but in which at least one of the substituents R1 to R4 must be Cl, which involves: reacting a hydroxy-pyrimidine or its tautomeric keto form with phosphoryl chloride in the presence of an amine or amine hydrochloride; recovering phosphoryl chloride after the reaction by adding phosphorus pentachloride and distilling the phosphoryl chloride; and separating the chloropyrimidine from the amine hydrochloride by addition of a solvent which will dissolve the chloropyrimidine but not the amine hydrochloride and removing the amine hydrochloride.
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- INDOL DERIVATIVES USEFUL FOR THE TREATMENT OF MIGRAINE, COMPOSITION AND UTILIZATION
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Indole derivatives having the Formula (I) wherein R1 is H, alkyl or acyl group; R2 is H, halogen or alkyl, hydroxy, alkoxy; ciano, carboxamide, carboxyl, alkoxicarbonyl, phenyl, phenyloxy or a group -(CH2)n-R6, (n=1-3), and R6 is a group ciano, nitro, phenyl, carboxyl, -CO2R7; -CONR7R8; -SO2NR7R8; -COR7; -SO2R7, R7 and R8 being H or alkyl; R7 and R8, together with N, can form a cycle of 4-7 links; R3, R4 and R5 are H, halogen or a group alkyl, phenyl, substituted phenyl, hydroxy, alcoxy, phenyloxy or benziloxy; NR11R12 is H or a group ciano, nitro, carboxyl, alcoxycarbonyl, carboxamido or a group R3; A is an alkyliden group -(CH2)-m, (m = 1-5), or alkenyl group; B is a piperazinoring (a), aminopyrrolidinoring (b); pyrrolidinamino ring (c); piperidinoring (d) or ethylendiamino -NR9-CH2-CH2-NR10-, R9 and R10 being H or an alkyl group. The compounds are useful for the treatment of migraine.
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- Process for the preparation of 5-(trifluoromethyl)-uracil, and the novel compounds 2,4-dichloro-5-trichloromethyl-pyrimidine and 2,4-difluoro-5-trifluoromethyl-pyrimidine
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5-Trifluoromethyl-uracil is obtained by chlorinating thymine under mild conditions, further chlorinating the resulting 2,4-dichloro-5-methyl-pyrimidine under drastic conditions to give 2,4-dichloro-5-trichloromethylpyrimidine, reacting the latter with a fluorinating agent to give 2,4-fluorinated and/or -chlorinated 5- trifluoromethylpyrimidines and subjecting these to hydrolysis. The novel chemical compounds 2,4-dichloro- 5-trichloromethylpyrimidine and 2,4-difluoro-5-trifluoromethylpyrimidine are obtained in the course of this process.
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- The facile synthesis of N(1),N(4)-dimethyl-5-substituted cytosines
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A facile, high yield synthesis of N(1),N(4)-dimethyl-5-alkyl (methyl, ethyl, n-propyl, n-butyl) cytosines has been described. This method seems to be an alternative and universal route to N(1),N(4)-methylated cytosines with any 5-substituent.
- Pluskota,Jankowski,Koroniak
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p. 2927 - 2934
(2007/10/02)
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