Pyrazines

Adding a certain compound to certain chemical reactions, such as: 41110-33-2, name is Methyl 5-methylpyrazine-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 41110-33-2, name: Methyl 5-methylpyrazine-2-carboxylate

A mixture of methyl 5-methylpyrazine-2-carboxylate (3.000 g, 19.7 17 mmol),1 -bromopyrrolidine-2,5-dione (NB S, 3.685 g, 20.703 mmol) and Azobisisobutyronitrile (AIBN, 1.295 g, 7.887 mmol) in carbon tetrachioride (20 mL) prepared at theroom temperature was heated at reflux for 10 hr, and cooled down to the ambient temperature. Then, water was added to the reaction mixture, followed by extraction withethyl acetate. The organic layer was washed with aqueous saturated sodium chloridesolution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residuewas chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 15 %) togive methyl 5-(bromomethyl)pyrazine-2-carboxylate as gray solid (1.500 g, 32.9 %).

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Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0293] (R)-(4-(4-((6-Bromoimidazo[1,2-a]pyrazin-8- yl)amino)phenyl)morpholin-2-yl)methanol XVII: In a 250 mL round bottom flask equipped with a condenser was placed 6,8-dibromoimidazo[1,2-a]pyrazine (2000 mg, 7.22 mmol) and added 30 mL isopropanol followed by N,N-diisopropylethylamine (2.52 ml, 14.44 mmol) and (R)-(4-(4-aminophenyl)morpholin-2-yl)methanol (1504.12 mg, 7.22 mmol). The reaction was heated to reflux (oil bath 95 C) overnight. The reaction was cooled and precipitates were collected by filtration and washed with isopropanol followed by hexanes to give the desired compound XVII, 2.92 g, 95% yield.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CLARKE, Astrid; CURRIE, Kevin, S.; DI PAOLO, Julie; KROPF, Jeffrey, E.; LEE, Seung, H.; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; SWAMINATHAN, Sundaramoorthi; XIONG, Jin-Ming; XU, Jianjun; ZHAO, Zhongdong; (169 pag.)WO2016/10809; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6164-79-0, A common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, 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.

To a stirred solution of sodium methoxide (25% in MeOH, 27.54 mL, 72.4 mmol, 1 eq) in 90 mL of toluene at 110 C. in a 3-neck flask attached with a mechanical stirrer, condenser and dropping funnel was added a solution of methylpyrazine-2-carboxylate (10 g, 72.4 mmol, 1 eq) in 115 mL of methyl acetate, dropwise, over a period of ?35-40 min. A yellow precipitate was formed. Stirring was continued at 110 C. for 3 hrs. The reaction was cooled and the yellow precipitate was filtered and washed with a small quantity of toluene. This solid was taken into 200 mL of saturated ammonium chloride and 400 mL of EtOAc. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 6.52 g (50%) of methyl 3-oxo-3-(pyrazin-2-yl)propanoate as a yellow solid.

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; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Jo; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/158066; (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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, A new synthetic method of this compound is introduced below., SDS of cas: 221136-66-9

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19847-12-2, These common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, 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.

General procedure: Cu(II)-NaY (0.1 g) was added to a mixture of benzonitrile (0.206 g, 2.0 mmol) and sodium azide (0.169 g, 2.6 mmol) in DMF (5 mL) and mixture was stirred at 120 C for 3 h. After completion of reaction (as monitored by TLC), the catalyst was centrifuged, washed with ethyl acetate and the centrifugate was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water and concentrated to give the crude solid crystalline 5-phenyltetrazole. The product was characterizedby 1H NMR , 13C NMR and mass spectroscopic analysis.

Statistics shows that Pyrazinecarbonitrile is playing an increasingly important role. we look forward to future research findings about 19847-12-2.

Reference:
Article; Sudhakar; Purna Chandra Rao; Prem Kumar; Suresh; Ravi; Asian Journal of Chemistry; vol. 29; 4; (2017); p. 864 – 866;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 143591-61-1,Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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 2 2-(3-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-ethanol 3-Bromo-8-chloro-imidazo[1,2-a]pyrazine (0.70 g, 3.0 mmol) (from Example 1 supra) was stirred in nBuOH (10 mL) and ethanolamine (0.22 mL, 3.65 mmol) followed by Hunig’s base (1.04 mL, 6.0 mmol) Reaction mixture was then heated at 100 C. overnight. The mixture was concentrated to dryness and water was added (150 mL) followed by a saturated aqueous solution of NaHCO3 (50 mL). The reaction was then extracted with EtOAc (3*20 mL) and the organic phases were combined, washed with water (2*20 mL), dried over MgSO4 and concentrated to dryness to give 2-(3-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-ethanol. (Yield 0.59 g, 77%). 1H (400 MHz; DMSO-d6) delta 3.52-3.56 (2H, m), 3.58-3.62 (2H, m), 4.79 (1H, t, J=5.4 Hz), 7.42 (2H, d, J=5 Hz), 7.56 (1H, d, J=5 Hz), 7.66 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Luk, Kin-Chun; Soth, Michael; US2012/238564; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

2-Chloro-3-aminomethylpyrazine HCl (2 g; 11.1 minol), (5)-(-)-l-(carbobenzyloxy)-2- piperidine carboxylic acid (3.2 g; 12.2 minol) and N,N-diisopropylethylamine (7.7 mL; 44.4 minol) were dissolved in dichloromethane (100 mL). N-[(dimethylamino)-lH-l,2,3-triazolo- [4,5-6]pyridin-l -ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) (6.3 g; 16.7 minol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was washed with aqueous sodium bicarbonate solution and water. The organic layer was then dried over sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed over S1O2 using a gradient of 20 -80% ethyl acetate in heptane to give 4.4 g; 11.3 minol of benzyl (2Patent; ACERTA PHARMA B.V.; BARF, Tjeerd; KAPTEIN, Allard; VERKAIK, Saskia; DEMONT, Dennis; COVEY, Todd; VAN DE KAR, Bas; VAN LITH, Bart; GULRAJANI, Michael; (166 pag.)WO2018/134786; (2018); 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. 33332-29-5, name is 2-Amino-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 33332-29-5

General procedure: To a solution of amines 12a-f in dichloromethane (20 mL) at 0 C was added triethylamine dropwise and the solution was stirred for 10 min. Methyl 2-(chlorosulfonyl)acetate in dichloromethane (10 mL) was added slowly at the same temperature. The reaction mixture was allowed to warm to room temperature and stirred for overnight after the addition completed. Water was added once the completion of reaction, and the mixture was stirred for 15 min. The organic layer was separated and dried over anhydrous sodium sulphate. Dried residue was evaporated under reduced pressure and was purified by flash column chromatography (silica gel, petroleum ether ramping to ethyl acetate:petroleum ether = 1:1) to give 13a-f.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33332-29-5.

Reference:
Article; Long, Yi; Yu, Mingfeng; Li, Peng; Islam, Saiful; Goh, Aik Wye; Kumarasiri, Malika; Wang, Shudong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5674 – 5678;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3, A common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

To 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74 g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 120 C. over the weekend. After cooling down to room temperature, DMF was removed under high vacuum. The residue was partitioned between EtOAc and water. The organic extracts were combined, dried and concentrated to give the crude product as a yellow solid (0.296 g, 93%), which was used in the subsequent reaction without further purification.

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 875781-43-4, A common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

2-Bromo-5H-pyrrolo [2,3-b] pyrazine (300 mg, 1.52 mmol) was dissolved in N, N- dimethylformamide (8 mL)Sodium hydride (60%, 91.3 mg, 2.28 mmol) was added under ice bath and stirring continued at this temperature. After 30 min 2- (trimethylsilyl) ethoxymethyl chloride (404 muL, 2.26 mmol ),Stir at room temperature for 12h. Quenched with water (20 mL)The mixture was extracted with dichloromethane (30 mL × 2) and concentrated for column chromatography (eluent: PE / EtOAc (v / v) = 5/1) to give 270 mg of a yellow oil. Yield: 54.3%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Bai Shun; Zhou Youbo; Yang Tiping; He Wei; Zhang Yingjun; Zheng Changchun; (103 pag.)CN106749268; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem