Category: 131860-97-4

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 131860-97-4, 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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows.

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:

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; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 131860-97-4

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

With the rapid development of chemical substances, we look forward to future research findings about 131860-97-4.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 131860-97-4, Adding some certain compound to certain chemical reactions, such as: 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate,molecular formula is C15H13ClN2O4, 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 131860-97-4.

A mixture of compound 6 (2.00 g, 6.24 mmol), Cs2CO3 (4.07 g, 12.48 mmol) and 2-cyanophenol (1.49 g, 12.48 mmol)in dry DMF (43 mL) was stirred at 85 C under nitrogen for 7 h. The resulting orange suspension was cooled to room temperature, poured into water and extracted with EtOAc. After evaporation of the solvent, the residue was purified by flash chromatography on silica gel using (hexane/EtOAc=4:1v/v) as eluent, to afford 7 (2.45 g, 97.5%); m.p. 115-116 C (lit.17 117-118 C); IR (KBr, numax/cm-1): 2230, 1707; 1H NMR: delta 8.43 (s, 1H), 7.75-7.67 (m, 2H), 7.52 (s, 1H), 7.44-7.32 (m,5H), 7.25 (d, 1H, J = 7.87 Hz), 6.44 (s, 1H), 3.78 (s, 3H), 3.66 (s, 3H); LC-MS (ESI): calcd for C22H18O5N3 ([M+H]+): 404.4; found: 404.1.

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:
Article; Liu, Yong-Gan; Luo, Yan; Lu, Yao; Journal of Chemical Research; vol. 39; 10; (2015); p. 586 – 589;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 131860-97-4, 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below.

Embodiment 20 (0104) This embodiment is provided to describe the method for preparing the azoxystrobin compound represented by formula (4) in a one-pot approach in the present invention. (0105) Under nitrogen protection, add 0.1 mol 4,6-dichloropyrimidine, 0.015 mol anhydrous potassium carbonate, 0.15 mol methyl formate, and 0.002 mol 2-methyl-1,4-diazabicyclo[2.2.2]-octane into 100 mL dimethyl benzene solution of 0.1 mol 3-(alpha-methoxy)methylene benzofuran-2-(3H)-ketone sequentially, start stirring, cool down to 5 C., and then control the temperature at 5-20 C., add 5 mL 29 wt. % methanol solution of sodium methoxide in droplets within 60 min., and then let the reaction proceed for 30 min. while stirring, to obtain a solid-containing mixture. Measured by GC, the content of the mixture of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate and methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 92%; measured by LC, the ratio of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate to methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 76:24. Next, distill out methyl formate and methanol under negative pressure; after the end of desolventizing under negative pressure, add 50 g water into the reaction bulb, stir so that the solid is dissolved, keep the solution still for stratification, and then condense the organic phase, to obtain viscous liquid. Add 0.003 mol dimethyl sulfate and 0.1 mol acetic anhydride into the obtained viscous liquid, heat up to 105 C., keep at the temperature and reflux, and let the reaction proceed for 60 min. Measured by GC, the content of the mixture of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate and methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 91%; measured by LC, the ratio of methyl 2-(2-((6-chloropyridinyl-4-)oxy)phenyl)-3,3-dimethoxyacrylate to methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate is 1.0:99; condense the reaction liquid under negative pressure to remove the solvent, to obtain viscous liquid compound methyl (E)-2-{2-[6-chloropyrimidinyl-4-oxy]phenyl}-3-methoxyacrylate. (0106) Add 80 ml butyl acetate, 0.085 mol 2-cyanophenol, 0.095 mol anhydrous potassium carbonate, and 0.003 mol 2,6-dimethyl-1,4-diazabicyclo[2.2.2]-octane into the obtained viscous liquid above, heat up the reaction mixture to 100 C. while stirring, keep at the temperature and let the reaction proceed for 250 min., and monitor the reaction situation with a gas chromatograph (GC). When the GC indicates that the normalized area of methyl (E)-2-[2-(6-chloropyrimidinyl-4-oxy)phenyl]-3-methoxyacrylate is smaller than 1%, add 50 ml water into the reaction system, stir for 10 min., keep the solution still for 10 min. at 80 C. for stratification, and then remove the aqueous phase, and repeat washing the organic phase once by adding water again; cool down the obtained organic phase to -5 C., so that crystals precipitate; then, filter to obtain a wet filer cake of azoxystrobin, rinse the filter cake with butyl acetate, and heat up the rinsed filter cake to approx. 50-60 C. with 50 ml methanol, beat and wash; then, filter and dry; thus, 28.1 g (0.0697 mol) light yellow solid is obtained, the purity is 99.6%, and the yield ratio is 69.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; NUTRICHEM COMPANY LIMITED; SHANGYU NUTRICHEM CO., LTD.; CHEN, Jianwei; WANG, Wenjun; CHI, Jianhong; ZHAO, Yongchang; DENG, Xufang; WANG, Long; JIN, Wentao; CHEN, Guobin; (15 pag.)US2016/200687; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.Product Details of 131860-97-4

To a solution of methyl (E)-2-{2-[6-chloropyrimidin~4-yloxy]phenyl} -3-methoxyacrylate (64.4g; prepared as described in WO 92/08703) in cyclohexanone (approximately 80g) was added 2-cyanophenol (26.6g) and cyclohexanone (26.6g). The mixture was heated to 5O0C and DABCO (0.2g) in cyclohexanone (2g) and potassium carbonate (42.4g) were charged. The reaction was heated to 9O0C and held for three hours. The temperature was adjusted to 50-600C and hot water (88g) added, stirred for 15 minutes, and the aqueous phase separated. Analysis of the cyclohexanone layer gave a 91.3% yield of methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin). Cyclohexanone was removed by vacuum distillation, and to the distillation residues at 8O0C was added methanol (59g). The methanol solution was cooled slowly to 0-50C, filtered and the cake washed with methanol (2×15.8g) to give, after drying, methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (87.0% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.Safety of (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

To a solution of methyl (E)-2-{2-[6-chloropyrimidin~4-yloxy]phenyl} -3-methoxyacrylate (64.4g; prepared as described in WO 92/08703) in cyclohexanone (approximately 80g) was added 2-cyanophenol (26.6g) and cyclohexanone (26.6g). The mixture was heated to 5O0C and DABCO (0.2g) in cyclohexanone (2g) and potassium carbonate (42.4g) were charged. The reaction was heated to 9O0C and held for three hours. The temperature was adjusted to 50-600C and hot water (88g) added, stirred for 15 minutes, and the aqueous phase separated. Analysis of the cyclohexanone layer gave a 91.3% yield of methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin). Cyclohexanone was removed by vacuum distillation, and to the distillation residues at 8O0C was added methanol (59g). The methanol solution was cooled slowly to 0-50C, filtered and the cake washed with methanol (2×15.8g) to give, after drying, methyl (E)- 2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (87.0% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2006/114572; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below., COA of Formula: C15H13ClN2O4

EXAMPLE 1 This Example illustrates the preparation of (E)-methyl 2-[2-(6-(2–cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (Compound No. 377 of Table I). (E)-Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.0 g), was treated with sodium methanethiolate (1.09 g) at room temperature in chloroform (15 ml) and water (10 ml) in the presence of a catalytic amount of tetrabutylammonium bromide. After stirring overnight, the chloroform layer was separated and the remaining aqueous layer was further extracted with chloroform. The combined chloroform layers were washed with water, dried and concentrated to give an orange oil. Chromatography using a mixture of ether and hexane (2:1) gave (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (0.92 g, 89% yield) as a pale yellow oil; 1H NMR: delta 2.52(3H,s), 3.59(3H,s), 3.73(3H,s), 6.55(1H,s), 7.17(1H,d), 7.20-7.55(3H,m), 7.45(1H,s), 8.57(1H,s) ppm.

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, 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; Clough, John Martin; Godfrey, Christopher Richard Ayles; Streeting, Ian Thomas; Cheetham, Rex; de Fraine, Paul John; Bartholomew, David; Eshelby, James John; US2003/60626; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, 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, Product Details of 131860-97-4, blongs to pyrimidines compound. Product Details of 131860-97-4

EXAMPLE 4 A solution of the potassium salt of 2-cyanophenol was prepared by mixing 2-cyanophenol (13.2 g) and potassium hydroxide (6.8 g) in water (7 g). This solution was added to (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) over 5 minutes while maintaining the temperature at 95-100 C. The resulting mixture was stirred at 120-20 C. for 2 hours. The reaction mixture was mixed with water and toluene and the organic layer separated. The toluene solution contained (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (61.5% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; ZENECA Limited; US6153750; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia