Category: 59489-71-3

Related Products of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

Concentrated H2SO4 (55 mL) was cooled to approximately 0 C. in a round-bottomed flask. NaNO2 (8.23 g, 119.3 mmol) was added portion-wise to the flask over approximately 5 min. After the addition was complete, the solution was allowed to mix and warm to ambient temperature over 30 min. The solution was cooled again in an ice bath, and a separate solution of the product from Part A (18.33 g, 105.3 mmol) in concentrated H2SO4 (90 mL) was added dropwise while maintaining a temperature of less than 10 C. After addition was complete, the solution was mixed in the ice bath for 15 min and then warmed to 40 C. for 15 min. The resulting mixture was allowed to cool to ambient temperature and then slowly poured into 500 g of ice. The resulting aqueous mixture was extracted with diethyl ether (3?500 mL). The organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to solids. The solids were slurried in hexanes (100 mL) at ambient temperature for approximately 1 hr, filtered, and desiccated to produce 9.55 g (51.8%) of solids.

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

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 59489-71-3, 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 59489-71-3 as follows.

General procedure: To a dioxane solution (6.0ml) of 2-amino-3,5-dibromopyrazine 7 (304mg, 1.20mmol) was successively added tetrakis(triphenylphosphine)palladium (112mg, 9.6×10-5mol, 8mol%), 4-trifluoromethylphenylboronic acid 8a (230mg, 1.21mmol), and 1ml of 2-moldm-3 sodium carbonate under argon atmosphere. The mixture was then refluxed for 4h under argon atmosphere. After cooling to room temperature, water (10ml) was added, and organic materials were extracted using chloroform (15ml×3). The combined organic layer was then dried over sodium sulfate. The removal of the solvent afforded brown solid, which was purified by preparative thin-layered chromatography on Merck silica gel (particle size, 5-40mum; 200×200×1.75mm, 5 plates) with a mixed solvent system (ethylacetate:hexane=8:3) as a mobile phase to give 9a (293mg, 77%) in the form of a pale yellow solid and 10a (17mg, 4%) in the form of a pale yellow solid.

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Saito, Ryota; Hirano, Takashi; Maki, Shojiro; Niwa, Haruki; Journal of Photochemistry and Photobiology A: Chemistry; vol. 293; (2014); p. 12 – 25;,
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

Application of 59489-71-3, The chemical industry reduces the impact on the environment during synthesis 59489-71-3, name is 2-Amino-5-bromopyrazine, I believe this compound will play a more active role in future production and life.

5-Bromopyrazin-2-amine (2.0 g, 11.49 mmol), (4-methylsulfonylphenyl)boronic acid (2.758 g, 13.79 mmol) and K3P04 (4.878 g, 22.98 mmol) were combined in MeCN (40 niL) / Water (10 mL) and Pd[P(tBu)3]2 (216 mg, 0.4227 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was triturated with water, then Et20 then dried in vacuo to give the sub-title compound as a beige solid which was used without further purification (2.53 g, 88% Yield). 3H NMR (400.0 MHz, DMSO) delta 3.20 (s, 3H), 6.80 (br s, 2H), 7.94 (d, 2H), 8.00 (d, 1H), 8.17 (d, 2H) and 8.64 (d, 1H) ppm.

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-Amino-5-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; YOUNG, Stephen, Clinton; STORCK, Pierre-Henri; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; PINDER, Joanne; WO2011/143423; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3, 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

2-amino-5-bromopyrazine (5.25g, 30mmol,1 eq.) and phenyl- boronic acid (5.5 g, 45mmol, 1.5 eq.) were dissolved in toluene (100 mL) and stirred at room temperature. Ethanol (20 mL) and 1 M Na2CO3 aq. (48 mL) were added to the reaction mixture. After vacuum deaeration and argon gas protection, bis-(triphenylphosphine) palladium(II) chloride (300 mg, 0.43 mmol, 5.5% of 2-amino-5-bromopyrazine) in 10 mL of toluene was added to the solution and the mixture was deaerated again and stirred for 2 hours at 105 C under argon atmosphere. After cooling to room temperature, the solution was filtered through a diatomite pad to remove the palladium catalyst. The solution was extracted with ethyl acetate, and the brown organic phase was washed with water and brine, dried over Na2SO4 and evaporated.The resulting residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate 1/1, v/v , affording 2-amino-5-phenylpyrazine (7) as a yellow solid (4.8g, 92.8%).1HNMR (DMSO-d6, 300 MHz): delta8.50 (s, 1H), 7.97 (s, 1H), 7.90 (d, 2H,J=7.8Hz), 7.44-7.39 (t, 2H), 7.32-7.28 (t, 1H), 6.55 (s,2H); ESI-MS calcd. for C10H9N3: 171.1, found: 173.2 (M+2H+).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-5-bromopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Ming-Liang; Jiang, Tian-Yu; Du, Lu-Pei; Li, Min-Yong; Chinese Chemical Letters; vol. 27; 4; (2016); p. 550 – 554;,
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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H4BrN3

Triisopropyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)silane (1.1 g, 2.9 mmol), 5-bromopyrazin-2-amine (507 mg, 2.9 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (64 mg, 0.087 mmol), 1M sodium carbonate (8.7 mL, 8.7 mmol), and dioxane (10 mL) were heated in a Biotage Emrys Optimizer microwave reactor at 120 C for 10 min. The reaction was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified using silica gel chromatography (0-100% ethyl acetate in hexanes) to give a tan solid (0.8 g, 80% yield).

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 59489-71-3.

Reference:
Article; Mortensen, Deborah S.; Perrin-Ninkovic, Sophie M.; Harris, Roy; Lee, Branden G.S.; Shevlin, Graziella; Hickman, Matt; Khambatta, Gody; Bisonette, Rene R.; Fultz, Kimberly E.; Sankar, Sabita; Bioorganic and Medicinal Chemistry Letters; vol. 21; 22; (2011); p. 6793 – 6799;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. COA of Formula: C4H4BrN3

EXAMPLE 1B 5-amino-2-pyrazinecarbonitrile A mixture of Example 1A (19.29 g, 105 mmol), freshly powdered KCN (16.9 g, 260 mmol), CuI (49.5 g, 260 mmol), 18-crown-6 (2.08 g, 7.8 mmol), and (PPh3)4Pd (1.8 g, 1.57 mmol) in N,N-dimethylformamide (600 mL) was stirred at room temperature for 30 minutes and heated to reflux in an oil bath preheated to about 200 C. The solution was stirred at reflux for 3 hours, cooled to room temperature, poured into ethyl acetate (1L), filtered through diatomaceous earth (Celite), treated with silica gel (100 g), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 11.9 g (94.4%) of the desired product. MS (APCI(+)) m/z 121 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.40 (d, J=0.7 Hz, 1H), 7.90 (d, J=0.7 Hz, 1H), 7.47-7.69 (br s, 2H).

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

Reference:
Patent; Li, Goaquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/34038; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59489-71-3, 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. 59489-71-3, name is 2-Amino-5-bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Into a 20-L 4-necked round-bottom flask was placed a solution of 5-bromopyrazin-2-amine (400 g, 2.30 mol) in ethylene glycol dimethyl ether (8 L) , iodocopper (131 g, 687.84 mmol) , diiodane (293 g, 1.15 mol) , iodopotassium (380 g, 2.29 mol) and 3-methylbutyl nitrite (1800 mL, 11.5 mol) . The resulting solution was stirred for 30 min at 60 C, then extracted with 2 x 10 L of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford the title compound.

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-Amino-5-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEBENHAM, John S.; COX, Jason M.; LAN, Ping; SUN, Zhongxiang; FENG, Zhe; SUN, Chunrui; SEGANISH, W. Michael; LAI, Zhong; ZHU, Chen; BARA, Thomas; RAJAGOPANALAN, Murali; DANG, Qun; KIM, Hyunjin M.; HU, Bin; HAO, Jinglai; (112 pag.)WO2018/107415; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. category: Pyrazines

EXAMPLE 41B 5-Bromo-2-iodopyrazine Under N2, to the mixture of the product of Example 41A (7.50 g, 43 mmol) in DME (anhydrous, Aldrich, 200 mL) was added CsI (Aldrich, 11.20 g, 43 mmol), iodine (Aldrich, 5.52 g, 21.6 mmol), CuI (Stream, 2.52 g, 13.2 mmol) and isoamyl nitrite (34.8 mL, 259.2 mmol) at ambient temperature. It was then heated to 60 C. and stirred for 30 min. till no gas evolution was observed. After being cooled down to room temperature, the dark mixtures was poured into a flask containing EtOAc (200 mL) and saturated NH4Cl (200 mL), stirred for 10 min. The organic layer was separated and the aqueous layer was extracted with EtOAc (2*1000 mL). The combined organic solution was washed with 5% of Na2S2O3 aqueous (2*50 mL), brine (50 mL) and dried over MgSO4. The drying agents were filtered off and the organic solution was concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) delta 8.50 (d, J=1.36 Hz, 1H), 8.62 (d, J=1.36 Hz, 1H) ppm; m/z 284 (M+H)+, 286 (M+H)+.

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

Reference:
Patent; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. SDS of cas: 59489-71-3

5-(thior)hen-3-yl)pvrazin-2-amine (N); In a dry 100 mL round bottom flask, a mixture of M (2.30 g, 13 mmol), thiopherie-3-boronic acid (2.54 g, 20.0 mmol), Pd(PPh3)4 (2.29 g, 2.0 mmol) and K2C03 (5.47 g, 40.0 mmol) in DMF (40 mL) was bubbled with N2 for 10 min, then the mixture was stirred at 100 C for 16 hours. The resulting mixture was evaporated to dryness. The residue was purified using column chromatography (silica gel, 2:1:7 hexane/CH2CI2/EtOAc). The fractions containing product were evaporated to dryness under vacuum to yield compound N as a light brown solid (1.63 g, 9.22 mmol, 71%). ¹H NMR (DMSO-d6, 300 MHz) No. 6.46 (bs, 2H), 7.55-7.65 (m, 2H), 7.85 (bs, 1 H), 7.90 (d, 1 H, J, 1.4), 8.42 (d, 1 H, J, 1.4).

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

Reference:
Patent; SUGEN, INC.; WO2005/113548; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem