Pyrimidines

Synthetic Route of 131860-97-4, 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, 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.

Example 1: In a 500 mL flask equipped with a magnetic stirrer, (E)-methyl 2-(2- ((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate (100 g, 97 % pure, 302 mmol), 2-hydroxybenzonitrile (41 g, 341 mmol) and potassium carbonate (25.08 g, 181 mmol) were added. Water (50 mL) and /V-methyl- piperidine (2.86 g, 28.8 mmol) were added at ambient temperature, then the mixture was placed on an oil bath at ambient temperature and heating begun. The mixture was heated to 120 C over 20 min and stirring begins once the external temperature is approx. 80 C. Some gas evolution was noted. The mixture was stirred at 100 C for 5 h, under a mild reflux. The mixture was then cooled to 80 C and diluted with ethyl acetate (200 mL) and then with water (100 mL). The two phases were stirred and separated. The upper organic portion was evaporated to dryness under vacuum at 40 C. The crude residue was dissolved in methanol (200 mL) at reflux, then water (30 mL) was added slowly at that temperature. The solution was allowed to cool freely with agitation to ambient temperature over lh and the solution was seeded with 0.4 g pure azoxystrobin at 40 C. The resulting slurry was further cooled to 0 C over 20 min, and held there for a further 20 min, then the solids were recovered by suction filtration and washed with 50 mL cold methanokwater 4: 1. The filter cake was dried under vacuum at ambient temperature overnight, affording the product azoxystrobin (114.68 g, 97% pure, 91.2 % yield) as a free flowing pale brown powder.

According to the analysis of related databases, 131860-97-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMINOVA A/S; LINDSAY, Karl Bernhard; WO2014/190997; (2014); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 49845-33-2

[00510] To a solution of 2,4-dichloro-5-nitropyrimidine (582 mg, 3 mmol) in THF (5 mL) wasadded DIEA (775 mg, 6 mmol) and tert-butyl3-aminophenylcarbamate (625 mg, 3 mmol, in 2mL THF) at -78 °C underN2 atmosphere. After stirring at -78 °C for 30 min, the reaction waswarmed up tor. t. and stirred overnight. The reaction was quenched with water (10 mL) andextracted with IPA/DCM (15:85) (5 mL X 3). The combined organic layer was washed withbrine, and dried over Na2S04. The solvents were removed under vacuum and the residue waspurified by flash chromatography (silica gel, 0 to 5percent ethyl acetate in PE/DCM (Ill) with 0.5percentTEA) to provide tert-butyl 3-(2-chloro-5-nitropyrimidin-4-ylamino )phenylcarbamate (1)(1.087g, 99percent) as an orange solid. LC-MS (ESI) m/z (M/M+2) 366.2/368.2.

The synthetic route of 49845-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; YAN, Shunqi; LOURY, David, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; WANG, Longcheng; WO2014/130693; (2014); 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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, 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. category: pyrimidines

To a solution of 2- chloro-5-fluoropyrimidine (10.0 g, 75.46 mmol, Sigma Aldrich) in DMF (100 mL) was added tributyl(vinyl)tin (31.1 g, 98.09 mmol) at RT. The reaction mixture was purged with N2for 5 min and Pd(PPh3)4(2.62 g, 2.26 mmol) was added. The reaction mixture was further degassed with N2for 5 min and stirred at 100 C for 24 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RTand quenched with water (100 mL). The aqueous layer was extracted with diethyl ether (2 x 100 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to obtain the initial product which was purified by silica gel chromatography (eluent: 6% EtOAc in hexanes) to provide 400.1 (8.0 g, 85% yield) as an oil.1H NMR (400 MHz, CDCl3) delta 8.58- 8.49 (m, 2H), 6.86 (dd, J = 17.4, 10.6 Hz, 1H), 6.53 (d, J = 17.3 Hz, 1H), 5.70 (d, J = 10.6 Hz, 1H). LCMS-ESI (pos.) m/z: = 125.1.

With the rapid development of chemical substances, we look forward to future research findings about 62802-42-0.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., Formula: C6H5ClN2O2

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-methyl-1,4-diazepane (0.144 mL, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25 C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (274 mg, 94%) as a white solid. This was used directly with no further purification. 1H NMR (399.9 MHz, DMSO-d6) delta 1.86-1.89 (2H, m), 2.26 (3H, s), 2.49-2.54 (2H, m, partially obscured by DMSO peak), 2.62-2.64 (2H, m), 3.81 (3H, s), 3.80-3.84 (2H, m), 3.89-3.91 (2H, m), 8.79 (2H, d). MS: m/z 251 (MH+)

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, 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
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Electric Literature of 130049-82-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 130049-82-0 as follows.

To a methanol (500 mL) solution, nitrogen was purged for 30 minutes to remove the nascent oxygen. 6-Fluoro-3-piperidin-4-yl-benzo[d]isoxazole Hydrochloride (50 g), 9-Hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido (1,2-a) pyrimidine-4-one (52 g) and triethylamine (55) were added and stirred at reflux for 30-32 hours. The reaction mixture was cooled to 25-35 C, and filtered off to yield paliperidone base. Yield: 75 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130049-82-0, its application will become more common.

Reference:
Patent; ORCHID CHEMICALS & PHARMACEUTICALS LIMITED; US2010/298566; (2010); A1;,
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Related Products of 89392-03-0, 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. 89392-03-0, name is Phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate, molecular formula is C13H13N3O4, 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.

5-Amino-2-dimethylaminocarbonyl-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide 0.6 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is added with stirring at 0 C. to a suspension of 1.0 g of 5-amino-2-dimethylaminocarbonylbenzene-sulfonamide and 1.1 g of 4,6-dimethoxy-2-(phenoxycarbonylamino)-pyrimidine in 10 ml of acetonitrile. The mixture is stirred again until complete reaction has taken place. Following the distillative removal of the volatile components, the residue is taken up in a little water and washed with diethyl ether. The aqueous phase is subsequently acidified with concentrated hydrochloric acid (pH=2-3). The deposited solid is washed with diisopropyl ether and then dried, to give 1.4 g of a solid which comprises the two compounds 5-amino-2-dimethylaminocarbonyl-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]-benzenesulfonamide and 5-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonylamino]-2-dimethylaminocarbonyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide in a ratio of about 2:1.

According to the analysis of related databases, 89392-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Schering AgrEvo GmbH; US6500952; (2002); B1;,
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Related Products of 302964-08-5 ,Some common heterocyclic compound, 302964-08-5, molecular formula is C16H13Cl2N5OS, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 24; Procedure for the Preparation of Dasatinib Form T1E2-1 (Hemi-Ethanolate)A mixture of compound 1 (591.4 mg, 1.5 mmol), N-(2-hydroxyethyl)piperazine (390.6 mg, 3 mmol) and N-ethyldiisopropylamine (0.525 ml, 3 mmol) in DMSO (1.5 ml) was stirred at 80 C. for 1.5 h. EtOH (10 ml) was added at the same temperature. The resulting solution was slowly cooled. The product started precipitating at 68 C. The mixture was cooled to room temperature. The product was filtered after 4 h, washed with EtOH (3×) and dried on the filter. Yield: 550 mg.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,302964-08-5, its application will become more common.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
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Synthetic Route of 663193-80-4 ,Some common heterocyclic compound, 663193-80-4, molecular formula is C4H3BrClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Intermediate (138.1 ): [1-(6-Amino-5-bromo^yrimidin-4-yl)-piperidin-4-yl]-(4-chloro- phenyl)-methanoneThe mixture of 5-bromo-6-chloro-pyrimidine-4-ylamine (2.0 g, 9.59 mmol, 1 .0 eq), 4- chlorophenyl-piperidin-4-yl-methanone (2.36 g, 10.55 mmol, 1 .10 eq) and potassium carbonate (6.63 g, 47.97 mmol, 5.0 eq) in DMF (5 ml_) was stirred at 50 C overnight. After pouring the reaction mixture to water, the precipitate was collected to give Intermediate (138.1 ). LC-MS (M+1 : 396, obsd: 396).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,663193-80-4, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; LAN, Rouxi; HUCK, Bayard R.; CHEN, Xiaoling; DESELM, Lizbeth Celeste; XIAO, Yufang; QIU, Hui; NEAGU, Constantin; MOCHALKIN, Igor; JOHNSON, Theresa L.; WO2013/40044; (2013); A1;,
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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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 113583-35-0

Example 2 Methyl 3-azido-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate 5.9 g (25 mmol) of methyl 3-azido-3-phenyl-2-hydroxybutyrate (Ex. 1) are dissolved in 80 ml of DMF, treated with 1.7 g (12.5 mmol) of potassium carbonate and 5.5 g (25 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and stirred for 6 hours at 50 C. and 12 hours at room temperature. The mixture is then poured onto 400 ml of water, and the precipitate formed is filtered off with suction, washed with water and dried. 6.3 g of a white powder are obtained. Yield: 67.2%, m.p.: 118-120 C.

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, 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; BASF Aktiengesellschaft; US5750469; (1998); A;,
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Adding a certain compound to certain chemical reactions, such as: 57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, 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, Recommanded Product: 5-Bromo-2-chloro-4-methoxypyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Bromo-2-chloro-4-methoxypyrimidine

To a solution of 5-bromo-2-chloro-4-methoxypyrimidine (Frontier Scientific, Logan, USA, 0.895 mmol) in THF (2.5 ml) cooled with an ice-bath was added a 2 M solution of ethylamine in MeOH (Aldrich, Buchs, Switzerland, 0.492 ml). The RM was stirred at 00C for 1 h and at rt for 66 h then the reaction mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (CH2CI2/iPr0H 0% to 6%) to give after evaporation of the fractions containing the title compound an off-white solid. (HPLC: tR 2.16min (Method C); M+H = 232, 234 MS-ES).

The synthetic route of 57054-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
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