Category: Pyrazines

Electric Literature of 446286-94-8, 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To asolution of dimethyl amino 3d (1370 mg, 6.82mmol) in drytetrahydrofuran (50 mL) under Ar at 80 C was slowly added1.57M n-butyllithium hydride (n-BuLi) in hexane (10.8 mL).After stirring for 60min at 80 C, to the mixture was addedN,N-dimethylformamide (DMF) (2.0 mL, 26mmol) and theresulting solution was allowed to warm to r.t. After stirring for1 h, to the reaction mixture was added water to decompose theexcess reducing agent. Further, to the mixed solution was addedwater followed by extraction with ethyl acetate (3 200 mL).The combined organic layers were dried over Na2SO4, filtered,and the solvents were removed under reduced pressure. Theresidue obtained was purified by silica gel column chromatography(hexane/ethyl acetate = 1/1) to yield arylaldehyde 4d (975 mg, 6.46mmol, 95%) as a light yellow solid: mp 112 C;IR (neat, , cm1): 2783, 1681, 1373, 1008; 1HNMR (500MHz, CDCl3) 9.91 (s, 1H), 8.69 (s, 1H), 8.08 (d, J = 1.1 Hz,1H), 3.26 (s, 6H); 13CNMR (126 MHz, CDCl3) 190.7, 155.5,144.3, 136.8, 129.4, 37.9; HR-ESI-MS: m/z: [M+ H]+ calculatedfor C7H10N3O, 152.0824; found, 152.0814.

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, 5-Bromo-N,N-dimethylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Saito, Ryohei; Kuchimaru, Takahiro; Higashi, Shoko; Lu, Shijia W.; Kiyama, Masahiro; Iwano, Satoshi; Obata, Rika; Hirano, Takashi; Kizaka-Kondoh, Shinae; Maki, Shojiro A.; Bulletin of the Chemical Society of Japan; vol. 92; 3; (2019); p. 608 – 618;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 36070-80-1 as follows. Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a solution of 5-chloropyrazine-2-carboxylic acid (500 mg, 3.1 mmol) and methyl-6- aminohexanoate hydrochloride (688 mg, 3.71 mmol) in dichloromethane (15 mL) was added 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide (71 1 mg, 3.71 mmol, 1.2 equiv). The reaction was allowed to stir for 18 hours at room temperature and was then diluted with dichloromethane (75 mL) and washed with 1 N hydrochloric acid (15 mL). The layers were separated, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and the residue was purified by flash column chromatography over silica gel (gradient elution with 20%-70% ethyl acetate in heptane) to provide methyl 6-{[(5-chloropyrazin-2-yl)carbonyl]- amino}hexanoate, 20 (378 mg, 43%), as a white solid. LCMS (Protocol E): m/z 308.2

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; DUSHIN, Russell George; ABRAMITE, Joseph A.; CASAVANT, Jeffrey M.; CHE, Ye; FILZEN, Gary Frederick; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; MOINE, Ludivine; O’DONNELL, Christopher John; ROBERTS, Lee; STARR, Jeremy; TUMEY, Lawrence N.; UCCELLO, Daniel P.; YOUNG, Jennifer; (135 pag.)WO2018/25168; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4430-75-5, The chemical industry reduces the impact on the environment during synthesis 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step A 2-(Octahydro-2H-pyrido[1,2-a]pyrazin-2-yl)acetonitrile 8 g of octahydro-2H-pyrido[1,2-a]pyrazine and 12 ml of acrylonitrile are refluxed for 48 hours in 150 ml of acetonitrile. The solvent is then removed in vacuo to yield 11 g of a pale yellow oil.

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, Octahydro-2H-pyrido[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Goldstein, Solo; Poissonnet, Guillaume; Parmentier, Jean-Gilles; Lestage, Pierre; Lockhart, Brian; US2003/195216; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6164-79-0,Some common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, 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.

Equimolar quantities (15 mmol) of (2) and the 85% hydrazine monohydrate were dissolved in anhydrous ethanol (25 mL) and vigorously stirred at 80 under oil bath for 4-5 h . The crude was precipitated from the solvent, collected using suction filtration and dried, and followed by recrystallization in ethanol.

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

Reference:
Article; Zhang, Fei; Wen, Qing; Wang, She-Feng; Shahla Karim, Baloch; Yang, Yu-Shun; Liu, Jia-Jia; Zhang, Wei-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 90 – 95;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Hydrazinopyrazine

2-((3 -(3 ,5-bis(trifluoromethyl)phenyl)- 1-1 ,2,4-triazol- 1 -yl)methyl)acrylic acid (0.2 g, 0.54 mmol) was dissolved in THE (10 mL) and cooled to 0 C. 2- hydrazinopyrazine (0.072 g, 0.65 mmol) followed by T3P (0.7 mL, 1.09 mmol) andDIPEA (0.4 mL, 2.19 mmol) was added dropwise at 0 C and stuffed for 1 h. The reaction mixture was concentrated under reduced pressure to afford 0.3 g of crude product, which was purified by chromatography (0-5% dichloromethane-methanol) to afford 10 mg of2-((3-(3, 5-bis(trifluoromethyl)phenyl)- 1H- 1,2, 4-triazol- 1 -yl)methyl)-N-(pyrazin-2-yl)acrylohydrazide (Yield: 4%). ?H NMR (400 MHz, DMSO-d6, ppm) = 10.34 (s,1H); 8.92 (s, 1H); 8.73 (s, 1H); 8.51 (s, 2H); 8.29 (s, 1H); 7.99 (s, 1H); 7.87-7.93 (m, 2H); 6.14 (s, 1H); 5.74 (s, 1H); 5.19 (s, 2H): LCMS for C18H14F6N70 [M+Hj:calculated 458.33; found 458.19.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; KATOLIEKE UNIVERSITEIT LEUVEN; SANDANAYAKA, Vincent, P.; SHECHTER, Sharon; DAELEMANS, Dirk; LEEN, Volker; DEHAEN, Wim, Alfons; SHACHAM, Sharon; WO2014/152263; (2014); 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

Reference of 5049-61-6, 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. 5049-61-6 name is Pyrazin-2-amine, This 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.

Step 1 ) Formation of 5-Bromopyrazin-2-amine N-bromosuccinimide (22.4 g, 0.126 mol) was added portionwise to a stirred solution of 2-Aminopyrazine (15 g, 157 mmol) in CCI4 (500 ml.) at O0C. The reaction mixture was stirred at RT under nitrogen atmosphere. After 3 hours, the reaction mixture was filtered and the filtrate was concentrated under vacuum. The crude material was purified by flash chromatography on silica (PE:EtOAc) to give the title compound as a yellow solid. LC/MS (Atlantis), M+(ESI): 173.8.1H-NMR (DMSO-d6, 400 MHz) delta 8.01 (1 H, s), 7.66-7.67 (1 H, s), 6.63 (2H, brs).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SERONO S.A.; SWINNEN, Dominique; JORAND-LEBRUN, Catherine; GRIPPI-VALLOTTON, Tania; GERBER, Patrick; GONZALEZ, Jerome; SHAW, Jeffrey; JEYAPRAKASHNARAYANAN, Seenisamy; WO2010/100144; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 122-05-4, The chemical industry reduces the impact on the environment during synthesis 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, I believe this compound will play a more active role in future production and life.

Example 42: Synthesis of (tetrakis(2′,6′-difluoro-2, 3′-bipyridinato)(mu-2,5-pyrazinedicarboxylate) diiridium(III), Abbreviation; [Ir(dfpypy)225PDC]2) [0408] [0409] Under argon atmosphere, into a 30 mL Schlenk flask equipped with a stirrer were placed 31 mg (0.15 mmol) of 2,5-pyrazinedicarboxylic acid, 16 mg (0.30 mmol) of sodium methoxide and 20 ml of methanol. And then, the mixture was reacted under stirring at room temperature for 2 hours. After the solvent was distilled off under reduced pressure, 184 mg (0.15 mmol) of di-mu-chloro-tetrakis(2′,6′-difluoro-2, 3′-bipyridinato) diiridium(III) and 25 ml of 2-ethoxyethanol were added to the residue, and then the resultant mixture was reacted under stirring at 110 C for 20 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. Subsequently, 30 ml of dichloromethane was added to the concentrate, and then the resultant mixture was filtered. The precipitate collected by filtration was washed with pure water, and then dried under reduced pressure, to provide 166 mg of tetrakis(2′,6′-difluoro-2, 3′-bipyridinato)(mu-2,5-pyrazinedicarboxylate) diiridium(III) as an orange solid. (84%) [0410] Additionally, tetrakis(2′,6′-difluoro-2, 3′-bipyridinato)(mu-2,5-pyrazinedicarboxylate) diiridium(III) had the following properties: [0411] 1H-NMR (400MHz, d-DMF, delta (ppm)); 8.64 (d, 2H), 8.51 (s, 2H), 8.46-8.24 (m, 6H), 8.17 (dt, 2H), 7.92 (dd, 2H), 7.73 (ddd, 2H), 7.15 (ddd, 2H), 6.01 (s, 2H), 5.50 (s, 2H) FD-MS (M/Z): 1316 M+

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, Pyrazine-2,5-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); 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. 14508-49-7, name is 2-Chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloropyrazine

General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

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 14508-49-7.

Reference:
Article; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; vol. 423; PART A; (2014); p. 11 – 15;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, 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 109-08-0, Safety of 2-Methylpyrazine

In the glove box,Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridinium](0.006mmol),Add 1.0 mL of toluene,After stirring for two hours,Add 1a (2mmol),Benzyl alcohol 2b (1mmol),After the reaction at 135 C for 48 hours, the reaction was stopped.Evaporate the solvent,Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3b.The product is a white solid.The yield was 63%.

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, 2-Methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem