Category: 13924-95-3

Adding a certain compound to certain chemical reactions, such as: 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, belongs to pyrazines compound, 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 13924-95-3, Recommanded Product: 13924-95-3

Preparation 415-Chloro-pyrazine-2-carboxylic acid methyl esterA mixture of 5-hydroxy-pyrazine-2-carboxylic acid methyl ester (Preparation 40, 50 g, 324mmol) and POCI3 (500ml_, 5.36mol) was heated under reflux for 1.5 hours and then poured onto ice. The resulting mixture was extracted with ether (4 chi 500ml_). The organic layers were concentrated in vacuo, and the residue was recrystallised from toluene to give the title compound (30.8g) in a 55% yield.

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.

Reference:
Patent; PFIZER LIMITED; COE, Jotham, Wadsworth; DEHNHARDT, Christoph, Martin; JONES, Peter; KORTUM, Steven Wade; SABNIS, Yogesh, Anil; WAKENHUT, Florian, Michel; WHITLOCK, Gavin, Alistair; WO2013/14567; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 13924-95-3

Step 1: (0546) To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100 C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methy-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H6N2O3

Potassium carbonate (8.82 g) and sodium chlorodifluoroacetate (6.53 g) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (3.3 g) in DMF (42.8 ml). The reaction solution was stirred at 100 C. for 30 minutes, and then saturated aqueous ammonium chloride was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and brine and then dried over magnesium sulfate. The drying agent was removed by filtration and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (928 mg).1H-NMR (400 MHz, CDCl3) delta (ppm): 4.04 (s, 3H), 7.49 (t, J=71.2 Hz, 1H), 8.47 (d, J=0.8 Hz, 1H), 8.92 (d, J=0.8 Hz, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, 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. Application In Synthesis of Methyl 5-hydroxypyrazine-2-carboxylate

Step 1 5-Bromo-pyrazine-2-carboxylic acid methyl ester A solution of 5-hydroxy-pyrazine-2-carboxylic acid methyl ester (2.56 g, 16.61 mmol) in phosphorous oxybromide 9.9 g, 34.9 mmol) were heated at 90 C. for 70 mins. The reaction was allowed to cool and the resulting solid carefully dissolved in methanol and then the solvent was evaporated in vacuo. The residue was partitioned between EtOAc and sat. NaHCO3 and the organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc:Hexanes 40:60) to afford the title compound. 1 H NMR (400 MHz, CDCl3) delta 9.06 (d, J=1.4 Hz,1H), 8.80 (d, J=1.4 Hz,1H), and 4.04 (s, 3H) ppm.

The synthetic route of Methyl 5-hydroxypyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5939439; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 13924-95-3

To a solution of methyl 5-hydroxypyrazine-2-carboxylate (9.25 g, 60.0 mmol) in /V,/V-dimethylformamide (120 mL) were added potassium carbonate (24.8 g, 179 mmol) and sodium chloro(difluoro)acetate (18.3 g, 120 mmol). The mixture was heated to 100 C for 15 minutes, whereupon it was filtered, and the filter cake was washed with ethyl acetate (2 x 50 mL). The combined filtrates were poured into saturated aqueous ammonium chloride solution (200 mL) and extracted with ethyl acetate (3 x 200 mL); the combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution (2 x 300 mL) and with saturated aqueous sodium chloride solution (2 x 300 mL), dried, filtered, and concentrated in vacuo. Chromatography on silica gel (Gradient: 0% to 15% ethyl acetate in petroleum ether) afforded the product as a yellow solid. Yield: 1 .7 g, 8.3 mmol, 14%. 1 H NMR (400 MHz, CDCI3) delta 8.92 (d, J=1 .2 Hz, 1 H), 8.47 (d, J=1 .2 Hz, 1 H), 7.49 (t, JHF=71 .3 HZ, 1 H), 4.04 (s, 3H).

According to the analysis of related databases, 13924-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13924-95-3,Some common heterocyclic compound, 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, molecular formula is C6H6N2O3, 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 9 6-Cyclopropylmethoxy-5-piperidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide a) 5-Methanesulfonyloxy-pyrazine-2-carboxylic acid methyl ester; A mixture of 3.34 g (22 mmol) methyl 5-hydroxypyrazine-2-carboxylate (commercially available), 2.73 g (24 mmol) methane sulfonyl chloride and 3.29 g (33 mmol) NEt3 in 40 mL DCM was stirred at room temperature for 4 h. Water and Na2CO3 was added and the organic layer was separated and dried with MgSO4. Evaporation yielded 3.7 g (73%) of the title compound which was used without further purification. 300-MHz-1H-NMR (DMSO): delta=9.06 (d, J=1.2 Hz, 1H, 3-H), 8.83 (d, J=1.2 Hz, 1H, 6-H), d=3.97 (s, 3H, OMe), 3.74 (s, 3H, SO2Me).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-hydroxypyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; Dietz, Michel; Gruener, Sabine; Hebeisen, Paul; Meyer Reigner, Sylvie C.; Nettekoven, Matthias; Puellmann, Bernd; Roever, Stephan; Ullmer, Christoph; US2008/85905; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H6N2O3

1) Synthesis of methyl 5-fluoromethoxypyrazine-2-carboxylateFluoromethyl toluene-4-sulfonate (Journal of Labelled Compounds and Radiopharmaceuticals, 46 (6), 555-566; 2003) (344 mg) and cesium carbonate (824 mg) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (130 mg) in DMF (2.0 mL). The reaction solution was stirred at 70C for 5 h and 30 min and then cooled to RT. Water was added to the reaction solution, followed by extraction with EtOAc. The organic layer was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (18.0 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 4.03 (s, 3H), 6.14 (d, J = 51.2 Hz, 2H), 8.42 (d, J = 1.2 Hz, IH), 8.94 (d, J = 1.2 Hz, IH).

According to the analysis of related databases, 13924-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; ELLARD, John Mark; FARTHING, Christopher Neil; HALL, Adrian; WO2011/9898; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C6H6N2O3

(62b) Methyl 5-Chloropyrazine-2-carboxylate Methyl 5-hydroxypyrazine-2-carboxylate (673 mg, 4.37 mmol) synthesised in Example (62a) was dissolved in phosphorous oxytrichloride (6.1 mL), and a few drops of N,N-dimethylformamide were added, followed by heating to reflux for 2 hours under nitrogen atmosphere. The reaction solution was poured into ice water, and extraction was carried out three times with chloroform (30 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 mL each), and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure to afford the desired compound (611 mg, yield 81%) as a gray solid. 1H-NMR (CDCl3, 400 MHz): delta 4.05 (3H, s), 8.71 (1H, d, J=1.6 Hz), 9.10 (1H, d, J=1.2 Hz).

The synthetic route of 13924-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2239253; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, belongs to pyrazines compound, 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 13924-95-3, Formula: C6H6N2O3

Preparation 415-Chloro-pyrazine-2-carboxylic acid methyl esterA mixture of 5-hydroxy-pyrazine-2-carboxylic acid methyl ester (Preparation 40, 50 g, 324mmol) and POCI3 (500ml_, 5.36mol) was heated under reflux for 1.5 hours and then poured onto ice. The resulting mixture was extracted with ether (4 chi 500ml_). The organic layers were concentrated in vacuo, and the residue was recrystallised from toluene to give the title compound (30.8g) in a 55% yield.

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.

Reference:
Patent; PFIZER LIMITED; COE, Jotham, Wadsworth; DEHNHARDT, Christoph, Martin; JONES, Peter; KORTUM, Steven Wade; SABNIS, Yogesh, Anil; WAKENHUT, Florian, Michel; WHITLOCK, Gavin, Alistair; WO2013/14567; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 13924-95-3, The chemical industry reduces the impact on the environment during synthesis 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

2-hydroxy-5-carbomethoxy-pyrazine (15.4 g) was dissolved in phosphorus oxychloride (100 ml) and several drops of dimethylformamide were added, followed by stirring with heating at 140C for 3 hours. After the reaction solution was poured into ice water and extracted with chloroform, the organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried and then concentrated. The resulting crystal was collected by filtration and washed with ether to obtain 2-chloro-5-carbomethoxy-pyrazine (14.0 g).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 5-hydroxypyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.