Pyrimidines

Electric Literature of 131860-97-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2; Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (£)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:

The chemical industry reduces the impact on the environment during synthesis 131860-97-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
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Synthetic Route of 3177-24-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
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Synthetic Route of 17573-78-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.17573-78-3, name is 4,5,6-Trifluoropyrimidine, molecular formula is C4HF3N2, molecular weight is 134.06, as common compound, the synthetic route is as follows.

Example (IV-1) Process e) 2.52 g (0.01 mol) of (5,6-dihydro-[1,4,2]oxathiazin-3-yl)-(2-hydroxyphenyl)-methanone O-methyloxime are dissolved in 10 ml of acetonitrile and admixed with 1.7 g (0.0123 mol) of potassium carbonate. The mixture is then cooled with stirring to 0 C., and 1.34 g (0.01 mol) of 4,5,6-trifluoropyrimidine are then added. Without further cooling, the mixture is stirred for another 12 hours. The solvent is then distilled off under reduced pressure and the residue is poured into water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.3 g (62% of theory) of [2-(5,6-difluoro-pyrimidine-4-yloxy)-phenyl]-(5,6-dihydro-[1,4,2]oxathiazin-3-yl)-methanone O-methyloxime. 1H NMR spectrum (CDCl3/TMS): delta=3.15/3.16/3.17/3.18 (2H); 3.83 (3H); 4.11/4.12/4.13/4.14 (2H); 7.26-7.53 (4H); 8.20 (1H) ppm.

The chemical industry reduces the impact on the environment during synthesis 17573-78-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Aktiengesellschaft; US6407097; (2002); B1;,
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Reference of 22536-66-9, Adding some certain compound to certain chemical reactions, such as: 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide,molecular formula is C5H4ClN3O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 22536-66-9.

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

According to the analysis of related databases, 22536-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14080-23-0, name is 2-Cyanopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14080-23-0

[0505] Synthesis of methyl pyrimidine-2-carboxylate:[0506] To a stirred solution of pyrimidine-2-carbonitrile (12.0 g, 114.28 mmol) in MeOH (20 mL) was added methanolic HC1 (180 mL) at 0 C and stirred for 16 h. After completion of starting material by TLC, the volatiles were evaporated under reduced pressure. The residue was neutralized with saturated NaHC03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was triturated with Hexane to afford methyl pyrimidine-2-carboxylate (10.0 g, crude) as yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 9.08 (d, 2H), 7.76 (t, 1H), 3.92 (s, 3H); LC-MS: 94.32%; 139 (M++l) (column; Chromolith RP-18, (100×4.6 mm); RT 2.85 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 70% EtOAc/Hexane (Rf: 0.2).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 14080-23-0, 2-Cyanopyrimidine.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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Synthetic Route of 1753-50-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below.

To a stirred solution of compound OE (0.80 g, 2.93 mmol) and 2-chloropyrimidine-5-carbonitrile (AF, 0.45 g, 3.22 mmol) in EtOH (10 mL), DIPEA (2.7 mL, 14.65 mmol) was added and the reaction mixture was stirred at 85 C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (40% EtOAc/hexane) to afford compound OF (0.82 g, 74.5%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): _ 9.01 (d, = 8.8 Hz, 1H), 8.64 (d, = 22.8 Hz, 2H), 7.85 (d, 7 = 18.0 Hz, 2H), 7.55-7.47 (m, 2H), 7.24-7.18 (m, 2H), 5.54-5.51 (m, 1H), 4.40-4.32 (m, 2H); LC-MS: m/z 376.8 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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Pyrimidine – Wikipedia

Related Products of 42965-55-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 42965-55-9, name is 5,6-Diaminopyrimidine-2,4(1H,3H)-dione sulfate. This compound has unique chemical properties. The synthetic route is as follows.

Example 72: 8-CycIopentyI-l-isobutyI-2-(2-methyI-pyridin-3-yIoxy)-l,7-dihydro- urin-6-one:; Step 1: 2,6-DichIoro-8-cyclopentyl-7H-purine:; A mixture of 5,6-diamino-lH-pyrimidine-2,4-dione sulphate (lOg, 70.42 mmol) and cyclopentanecarboxylic acid (8.02g, 70.42 mmol) was taken in POCI3 and stirred at reflux temperature for 3 days under inert conditions. Reaction mixture wasconcentrated and quenched with water and extracted with ethyl acetate. Ethyl acetate layer was washed with brine and water, dried over anhydrous sodium sulphate and concentrated. Residue obtained was purified by coloumn chromatography to provide 2,6-dichloro-8-cyclopentyl-7H-purine (3.5 g, 20 %) as brown solid.’HNMR(400MHz, CDC13): delta 1.25-1.81 (m, 2H); 1.85-1.93 (m, 2H); 1.98-2.07 (m, 2H); 2.20-2.25 (m, 2H); 3.42-3.45 (m, 1H); 1 1.50 (s, 1H).

According to the analysis of related databases, 42965-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADVINUS THERAPEUTICS PRIVATE LIMITED; RAMDAS, Vidya; KOUL, Summon; BASU, Sujay; WAMAN, Yogesh; SHEJUL, Yogesh; BARAWKAR, Dinesh; PALLE, Venkata Poornapragnacharyulu; WO2011/55391; (2011); A1;,
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Application of 4595-61-3, Adding some certain compound to certain chemical reactions, such as: 4595-61-3, name is Pyrimidine-5-carboxylic acid,molecular formula is C5H4N2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4595-61-3.

Into a solution of the above amine (0.050 g, 0.13 mmol), pyrimidine-5-carboxylic acid (0.017 g, 0.14 mmol) and 1-hydroxybenzotriazole hydrate (0.008 g, 0.05 mmol) in THF (1.3 mL) was added triethylamine (0.019 g, 0.19 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.034 g, 0.018 mmol). After stirring overnight, the reaction mixture was diluted with ethyl acetate and washed with 5percent sodium bicarbonate, and then with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel chromatography eluted with 1-9percent methanol in methylene chloride to provide the title compound. LRMS (ES, M+H+): 503 1H NMR (CD3OD): delta 9.32 (s, 1H), 9.29 (s, 2H), 8.22 (bs, 1H), 7.91 (bd, J=8 Hz, 1H), 7.67 (bd, J=8 Hz, 1H), 7.55 (dt, J=8 and 5.6 Hz, 1H), 7.49 (m, 2H), 7.24 (m, 2H), 7.15 (m, 2H), 4.69 (s, 2H), 3.69 (s, 3H).

According to the analysis of related databases, 4595-61-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bock, Mark G.; Kuduk, Scott D.; Wood, Michael R.; US2006/106011; (2006); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 90905-33-2, name is 2-Methylpyrimidine-5-carbaldehyde, molecular formula is C6H6N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H6N2O

To a stirred solution of N1-cyclopropyl-5-fluorobenzene-1,2-diamine Int-1 (200 mg, 1.20 mmol) in DMF (2 mL) and water (0.2 mL) under an inert atmosphere was added 2-methylpyrimidine-5-carbaldehyde (176 mg, 1.44 mmol) and oxone (364 mg, 2.40 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 2percent MeOH/CH2Cl2) to afford 1-cyclopropyl-6-fluoro-2-(2-methylpyrimidin-5-yl)-1H-benzo[d]imidazole Ex. 20 (70 mg, 0.26 mmol, 22percent) as an off white solid. ?H NMR (400 MHz, CD3OD): oe 9.27 (s, 2H), 7.69 (dd, J=8.8, 4.8 Hz, 1H), 7.48 (dd, J=8.9, 2.4 Hz, 1H), 7.16-7.07 (m, 1H), 3.81-3.75 (m, 1H), 2.81 (s, 3H), 1.27-1.19 (m, 2H), 0.83-0.78 (m, 2H). EC-MS: m/z 269 [M+H] at 2.24 RT (99.87percentpurity). HPEC: 99.35percent.

With the rapid development of chemical substances, we look forward to future research findings about 90905-33-2.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10320-42-0, 2-Chloro-5-nitropyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 10320-42-0, blongs to pyrimidines compound. HPLC of Formula: C4H2ClN3O2

EXAMPLE 47; (S)-2-(4-Chlorophenyl)-5-(2-(3-(methylamino)pyrrolidin-l-yl)pyrimidin-5-yl)-4,5- dihydropyrrolo[3,4-c]pyrazol-6(2H)-one; Example 47 A. (5)-N-Methyl- 1 -(5 -nitropyrimidin-2-yl)pyrrolidin-3 -amine; [00229] (S)-N-Methylpyrrolidin-3 -amine (286 mg, 2.86 mmol) was added to 2- chloro-5-nitropyrimidine (415 mg, 2.60 mmol) slowly (CAUTION: extreme exotherm. . .). The resulting mixture was heated at 110 0C for 10 min. After cooling down to room temperature, another portion of amine (0.100 g) was added to the reaction mixture. The resulting mixture was heated at 110 0C for 10 min. After cooling down to room temperature, the obtained black solid product (Example 47A) was used for next step without further purification. LCMS (ES): m/z 252.3 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10320-42-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; WASHBURN, William, N.; WANG, Wei; HERNANDEZ, Andres; AHMAD, Saleem; ZHAO, Guohua; WO2010/47956; (2010); A1;,
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