Category: 27825-20-3

Related Products of 27825-20-3,Some common heterocyclic compound, 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, 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.

(1) 308 g (2 mol, 1 eq) of methyl 3-hydroxy-2-pyrazinecarboxylate and 956 g (6 mol, 3 eq) of liquid bromine were added to 4 L of acetonitrile,The mixture was stirred at 27 C for one hour,TLC detection reaction completely,The reaction solution was poured into 4 L of water,The excess liquid bromine was removed with a saturated aqueous solution of sodium sulfite,Standing filter,Filter cake vacuum drying at room temperature,300 g of the product methyl 6-bromo-3-hydroxy-2-pyrazinecarboxylate (including its tautomer 6-bromo-3-oxo-3,4-dihydro-2-pyrazinecarboxylic acid Methyl ester),Yield 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-Hydroxy-2-pyrazinecarboxylate, its application will become more common.

Reference:
Patent; Qingdao Hangdao District Chinese Medicine Hospital; Lu, Yanmin; (5 pag.)CN105732524; (2016); A;,
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. 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-Hydroxy-2-pyrazinecarboxylate

458 g (3 mol, 1 eq) of methyl 3-hydroxy-2-pyrazinecarboxylate and 532 g (3 mol, 1 eq) Bromosuccinimide were successively added to 5 L of acetonitrile,The mixture was stirred at 25 C for 12 hours,After TLC detection reaction was complete,The reaction was stopped,filter,Filter cake vacuum drying at room temperature,To give 554 g of methyl 6-bromo-3-hydroxy-2-pyrazinecarboxylate (including tautomer 6-bromo-3-oxo-3,4-dihydro-2-pyrazinecarboxylic acid Methyl ester),The yield was 85%. 6-Bromo-3-hydroxy-2-pyrazinecarboxylic acid methyl ester

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; Qingdao Hangdao District Chinese Medicine Hospital; Lu, Yanmin; (5 pag.)CN105732524; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 27825-20-3, 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 27825-20-3 as follows.

3-Hydroxypyrazine-2-carboxylic acid methyl ester (1 g, 6.49 mmol, 1 eq.) Was added to a suspension of sodium hydride (60%, 259 mg, 6.49 mmol, 1 eq.DMF (50 mL). The reaction solution was stirred at room temperature for 1 h and then (3,3-dimethoxycyclobutyl) methylmethanesulfonate(1.46 g, 6.49 mmol, 1 eq.) Was added and the mixture was stirred at 130 & lt; 0 & gt; C for 18 h. After completion of the reaction, the mixture was diluted with 50 mL of waterThe mixture was extracted with EtOAc (60 mL x 2) and the organic phase was washed with saturated sodium chloride solution (60 mL x 2), dried over anhydrous sodium sulfate,Filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: PE / EtOAc (v / v) = 3/1) to give the title compound as a white solid(220 mg, 54%).

According to the analysis of related databases, 27825-20-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd. of Guangdong; Ren, Qingyun; Luo, Huichao; Tang, Changhua; Zhang, Jiancun; Zhang, Yingjun; (30 pag.)CN104447583; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27825-20-3, 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. 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 99 methyl 3-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methoxy)pyrazine-2-carboxylate; [00197J l-(3-fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate XXIII,1.0 mmol) and methyl 3-hydroxypyrazine-2-carboxylate (1.0 mmol) were dissolved in N- methylpyrrolidinone (3 ml) and K2CO3 (1.1 eq) was added. The mixture was stirred overnight. 20 ml water was added and the product was extracted three times with dichloromethane. The organic was dried over Na?SCu, filtered, and concentrated. The crude was purified by column chromatography using 0-70% gradient of saturated ammonia/MeOH and dichloromethane. 1H NMR (400 MHz, DMSOd6): ¡ì 10.73 (s, IH), 7.89 (d, IH), 7.40 (d, IH), 7.35 (m, IH), 6.95-7.10 (m, 3H), 6.94 (m, 2H), 5.04 (s, 2H), 4.31 (d, 2H), 3.79 (s, 3H). MS (ES+): M/Z 418 (M+l).

The synthetic route of Methyl 3-Hydroxy-2-pyrazinecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REPLIDYNE, INC.; WO2008/11191; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, 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 27825-20-3, Recommanded Product: Methyl 3-Hydroxy-2-pyrazinecarboxylate

Reference Example 27 0.30 g of methyl 3-hydroxy-2-pyrazinecarboxylate was dissolved in 1.5 ML of dimethyl sulfoxide, and thereafter, 0.70 ML of triethylamine and 0.54 g of L-aspartic acid diethyl ester hydrochloride were successively added thereto, followed by stirring at room temperature for 8 hours.. After chloroform and water were added to the reaction solution, the mixture was adjusted to PH 2 with 2 mol/L hydrochloric acid, and the organic layer was separated.. The obtained organic layer was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure.. Toluene and n-hexane were added to the obtained residue, and the precipitate was collected by filtration, so as to obtain 0.18 g of diethyl (2S)-2-{[(3-hydroxy-2-pyrazinyl)carbonyl]amino} butanedioate.1H-NMR(CDCl3)delta: 1.27(3H,t,J=7.2Hz), 1.30(3H,t,J=7Hz), 2.94(1H,dd,J=4.4,17.2Hz), 3.15(1H,dd,J=4.8,17.2Hz), 4.14-4.23(2H,m), 4.24-4.32(2H,m), 4.99-5.02(1H,m), 8.15(1H,d,J=2.6Hz), 8.40(1H,d,J=1.5Hz), 8.78(1H,d,J=5.9Hz), 12.4(1H,brs)

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; TOYAMA CHEMICAL CO., LTD.; EP1417967; (2004); 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. 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 27825-20-3

1.52 g of methyl 3-hydroxy-2-pyrazinecarboxylate was suspended in 12.2 mL of 1,1,1,3,3,3-hexamethyldisilazane, and the suspension was heated under reflux for 1 hour. After standing to cool, the solvent was removed under reduced pressure, and the obtained residue was dissolved in 30 mL of dichloroethane under nitrogen atmosphere. 4.98 g of beta-D-ribofuranose-1-acetate-2,3,5-tribenzoate and 1.73 mL of tin(IV) chloride were successively added thereto, and the mixture was further stirred at room temperature for 14 hours. The reaction mixture was diluted with 30 mL of chloroform and 30 mL of a saturated sodium bicarbonate aqueous solution, and the precipitate was removed by filtration, so that the organic layer was obtained. The obtained organic layer was successively washed with water and then with a saturated saline solution. Thereafter, the layer was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluant; n-hexane : ethyl acetate = 1 : 1], so as to obtain 3.4 g of a white solid, methyl 4-{(2R, 3R, 4R, 5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. IR(KBr)cm-1: 1734, 16601H-NMR(CDCl3)delta: 3.96(3H,s), 4.71(1H,dd,J=4.0,12.4Hz), 4.8-4.9(2H,m), 5.8-5.9(2H,m), 6.45(1H,d,J=4.0Hz), 7.34(1H,d,J=4.2Hz), 7.3-7.6(9H,m), 7.70(1H,d,J=4.2Hz), 7.9-8.0(4H,m), 8.0-8.1(2H,m); Reference Example 20 [136.1] 50 mg of methyl 3-hydroxy-2-pyrazinecarboxylate was suspended in 1.6 mL of 1,1,1,3,3,3-hexamethyldisilazane, and the solution was heated under reflux for 1 hour under nitrogen atmosphere. After standing to cool, the solvent was removed under reduced pressure, and an acetonitrile solution containing 0.17 g of (2S, 3R, 4R, 5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[2-(diethoxyphosphoryl)ethyl]tetrahydro-3-furanyl benzoate was added thereto. Thereafter, the solvent was removed under reduced pressure. The obtained residue was suspended in 2.00 mL of acetonitrile under nitrogen atmosphere, and thereafter, 67 muL of tin(IV) chloride was added thereto under ice cooling, followed by leaving at room temperature for 24 hours. 300 mg of methyl 3-hydroxy-2-pyrazinecarboxylate was treated in the same above manner, and the obtained reaction mixture was poured into a mixed solution of 50 mL of ethyl acetate, 50 mL of ice and 100 mL of a saturated sodium bicarbonate aqueous solution. The precipitate was removed by filtration, the organic layers were separated, and the aqueous layer was extracted with 50 mL of ethyl acetate. The organic layers were combined, and the obtained organic layers were washed with a saturated saline solution and then dried with anhydrous magnesium sulfate. The solvent was then removed under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluant; ethyl acetate : methanol = 100 : 1], so as to obtain 0.76 g of a colorless oil product, methyl 4-{(2R, 3R, 4R, 5R)-3,4-bis(benzoyloxy)-5-[2-(diethoxyphosphoryl)ethyl]tetrahydro-2-furanyl}-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. IR(neat)cm-1: 1734, 16701H-NMR(CDCl3)delta: 1.3-1.35(6H,m), 1.85-2.3(4H,m), 3.97(3H,s), 4.05-4.2(4H,m), 4.45-4.55(1H,m), 5.65(1H,t,J=6.5Hz), 5.74(1H,dd,J=3.6,5.9Hz), 6.24(1H,d,J=3.6Hz), 7.3-7.4(4H,m), 7.5-7.6(4H,m), 7.85-7.95(4H,m).

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; TOYAMA CHEMICAL CO., LTD.; EP1417967; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, 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. 27825-20-3

EXAMPLE 19 In 5 mL of dimethyl sulfoxide is dissolved 0.42 g of L-alanyl-L-alanine trifluoroacetate. Then, 1.07 mL of triethylamine and 0.71 g of methyl 3-hydroxy-2-pyrazinecarboxylate are successively added to the solution, which is then stirred at 40 C. for 17 hours. The solvent is distilled off under reduced pressure, and 2 mL of water was added to the residue thus obtained. The deposited product is collected by filtration and purified by column chromatography [eluent: chloroform:methanol =30:1) to obtain 0.035 g of (2S)-2-[((2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)carbonyl]amino}-propanoyl)amino]propanoic acid. IR(KBr) cm-1: 1665, 1675, 1655 NMR(DMSO-d6) delta value: 1.28(3H,d,J=7 Hz), 1.32(3H,d,J=7 Hz), 3.95-4.95(2H,m), 5.1(2H,brs), 7.71(1H,d,J=3 Hz), 7.87(1H,d,J=3 Hz), 8.32(1H,d,J=7 Hz), 9.9(1H,brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27825-20-3, its application will become more common.

Reference:
Patent; Furuta, Yousuke; Egawa, Hiroyuki; Nomura, Nobuhiko; US2002/13316; (2002); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem