Category: 6863-73-6

These common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, 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. category: Pyrazines

8-Chloroimidazor 1 ,2-alpyrazine[00237] 2-Bromo-l,l-diethoxyethane (6.21 mL, 0.041 mmol) was added to a mixture of 48% HBr (aq.) solution (1.64 mL) and water (20 mL) and the resulting mixture was stirred under reflux for 1 hour. The reaction mixture was then allowed to cool and washed with brine (2 x 30 mL), dried (MgSO4) and carefully concentrated in vacuo. The resulting oil was dissolved in 1 ,2-dimethoxoethane (20 mL) and added to a suspension of 2-amino-3 -chloro- pyrazine (2.142 g, 0.016 mmol) in 1 ,2-dimethoxoethane (30 mL). 48 % HBr (aq.) solution (0.313 mL) was then added and the resulting mixture was stirred under reflux for 1 hour. Upon cooling a precipitate formed which was collected by filtration and washed with diethyl ether to give the crude HBr salt. This was dissolved in NaHCO3 (aq.) and extracted into DCM. Drying of the organic layer (MgSO4) followed by concentration in vacuo provided the title compound (1.9 g, 75%) as a yellow/pale brown solid. 1H NMR (d6-DMSO): 8.68-8.64 (IH, br m), 8.30-8.26 (IH, br m), 7.88-7.85 (IH, br m), 7.75-7.70 (IH, br m).

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

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6863-73-6, A common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, molecular formula is C4H4ClN3, 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.

Benzyl alcohol (4.55 g, 42.15 mmol) was added under an inert atmosphere dropwise to a suspension of sodium hydride (1. 01 g, 42.13 mmol, 80%) in N-methylpyrrolidinone. Stirring of the reaction mixture was continued for 30 min. 2-Amino-3-chloropyrazine (Compound I in Scheme 1, 5.0 g, 38.6 mmol) was then added in incrememtal portions and the resultant mixture was heated at 80 C for 24 h. The reaction mixture was subsequently cooled and water (200 mL) was added. The aqueous solution was extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with water (2 x 100 mL), dried (Mg04), and concentrated under reduced pressure to obtain a light brown residue. Addition of cold water to the residue, triggered crystallization of the desired product. The crystals were collected and dried over P2O5 (6.33 g, 82%). 1H-NMR (CDCl3) No. 7. 54 (d, J 3.1 Hz, 1H), 7.45-7. 32 (m, 6H), 5. 38 (s, 2H), 4. 78 (br s, 2H); MS (ESI) 202.2 ([M+H] +)

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; CARDIOME PHARMA CORPORATION; WO2005/34837; (2005); A2;,
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. 6863-73-6, name is 3-Chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6863-73-6

Example A3 8-Chloro-imidazo[1,2-a]pyrazine Bromoacetaldehyde diethyl acetal (17.4 ml, 115.8 mmol) was added dropwise to a 48% aqueous solution of hydrobromic acid (4.45 ml, 38.6 mmol) at RT. The mixture was stirred at reflux temperature for 2 h. and then poured onto a suspension of sodium hydrogen carbonate (74.5 g, 0.88 mol) in isopropanol (220 ml). The mixture was stirred for a further 30 min. and then filtered off. 3-Chloro-pyrazin-2-ylamine (5 g, 38.6 mmol) was added to the filtrate and the mixture was stirred at 85 C. for 4 h. The solvent was evaporated in vacuo and the crude product suspended in a saturated solution of sodium hydrogen carbonate and extracted with DCM. The organic layer was dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et2O to yield intermediate 3 (4.1 g, 70%) as a brown solid which was used in the next step without further purification.

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 6863-73-6.

Reference:
Patent; Janssen Pharmaceutica NV; US2012/329792; (2012); 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. 6863-73-6, name is 3-Chloropyrazin-2-amine, A new synthetic method of this compound is introduced below., SDS of cas: 6863-73-6

General procedure: Sodium hydride (60% in mineral oil, 0.04 g, 1 mmol) was addedto a stirred solution of benzyl alcohol derivative (1 mmol) inanhydrous N,N-dimethylformamide (3 mL of DMF) at room temperatureand stirring was continued for 1 h. 2-Amino-3-chloropyrazine (8b, 0.13 g, 1 mmol) was added to the reactionmixture and the reaction mixture was stirred at 100 C for 15 h.After cooling, the solvent was evaporated and the residue waspartitioned betweenwater and dichloromethane. The organic layer was dried over sodium sulfate anhydrous, filtered, and concentrated.The residue was purified by column chromatography (SiO2,EA/n-Hex 1/5). 4.1.2.1 3-(Benzyloxy)pyrazin-2-amine (9g) Yellow solid, yield: 53.8%, 1H NMR (400?MHz, CDCl3) delta?=?5.45 (2H, s, OCH2Ph), 6.20 (2H, br, NH2), 7.38-7.48 (7H, m, ArH). Reported [ 48,49].

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 529 – 543;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6863-73-6, name is 3-Chloropyrazin-2-amine, 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 6863-73-6, HPLC of Formula: C4H4ClN3

2-Amino-3-chloropyrazine 9 (10.0 g, 77.2 mmol) was added to a stirred suspension of NCS (11.6 g, 86.9 mmol) in chloroform (73 mL). The reaction mixture was heated at reflux for 4 h. The solution was cooled and partitioned between chloroform (180 mL) and water (2*50 mL). The organic layer was dried, filtered and concentrated. Flash chromatography on silica, eluting with chloroform, gave 10 (9.66 g, 76%) as a pale yellow solid. Mp 200-202 C; Rf (CHCl3) 0.32; numax (thin film/cm-1) 3411 (NH2), 3019 (Ar CH); (found: C, 28.89; H, 1.71; N, 24.99; C4H3N3Cl2: 0.125(H2O) requires C, 28.90; H, 1.97; N, 25.28%); deltaH (500 MHz; CDCl3) 4.96 (2H, br s, NH2), 7.90 (1H, s, 6-H); deltaC (125 MHz; CDCl3) 131.4, 134.6, 140.0, 150.3; GC-MS m/z 167, 165, 163 (M+), GC tR 2.51 min; purity 98%; HRMS (found: MH+ m/z 163.9782; requires 163.9777).

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:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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 6863-73-6 as follows. Recommanded Product: 6863-73-6

[0665] A 3-necked 250 mL round-bottomed flask was charged with cesium carbonate (22.64 g, 69.5 mmol), 2-amino-3-chloropyrazine (3 g, 23.16 mmol, Synchem Inc., Elk Grove Village, IL), and {1,1′-bis(diphenylphosphino)ferrocene} dichloropalladium(II) (1.69 g, 2.32 mmol, Strem Chemicals, Newburyport, MA). A reflux condenser was attached, and the apparatus was sealed. The vessel was evacuated and backfilled with nitrogen. DMF (66.2 mL) was added, followed by triethylborane (1.0 M in THF; 42 mL, 42 mmol; Sigma-Aldrich Corporation, St. Louis, MO, USA). The reaction was then stirred in a pre-heated 90 C oil bath for 1 h. The reaction mixture was cooled to rt, water was added, and the resulting mixture was extracted with DCM (2). The combined extracts were dried over MgSO4 and concentrated in vacuo. The crude residue was taken up in MeOH and loaded onto a column composed of Si- propylsulfonic acid (Silicyle). The column was flushed with 4 column volumes of MeOH before eluting the title compound with 4 column volumes of 2M ammonia in MeOH. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography (eluent: 0-20% 2 M NH3 in MeOH/DCM) to provide 3-ethylpyrazin-2-amine (Intermediate I- 19, 2.34 g, 19.0 mmol, 82 % yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) d ppm 7.75 (d, J=2.70 Hz, 1H) 7.65 (d, J=2.70 Hz, 1H) 6.13 (br s, 2 H) 2.60 (q, J=7.39 Hz, 2 H) 1.17 (t, J=7.46 Hz, 3 H).

According to the analysis of related databases, 6863-73-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6863-73-6, A common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, molecular formula is C4H4ClN3, 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.

alpha-Bromo diethyl acetal (51.6 mL, 332.7 mmol, 2.5 eq) was added to a solution of 7.7 mL HBr (conc.) and 80 mL of H2O. The reaction was heated at reflux for 1 h. The reaction was cooled and extracted 2× with Et2O (200 mL). The Et2O extracts were combined, washed with brine, and dried over Na2SO4 before being concentrated. The material was not left on the rotavap for an extended time or put under high vacuum. The oily residue was mixed with DME (200 mL) and the 2-amino-3-chloropyrazine (2, 17.240 g, 133.1 mmol) was added. HBr conc. (1-1.5 mL) was added and the reaction was heated at reflux. The reaction is heterogeneous reaction mixture, becomes homogenous after 10-15 minutes. After approximately 30 minutes a precipitate begins to form. After 1 hour at reflux the black reaction was cooled to room temperature, filtered, and washed with Et2O (4×, 75 mL) to give compound 101 1H NMR (DMSO-d6, 400 MHz) 8.70 (d, J=2.0 Hz, 1H), 8.32 (s, 1H), 7.93 (s, 1H), 7.79 (d, J=3.0 Hz, 1H). LC/MS shows a mixture of two products (one product by LC and two by MS). By MS there is a mass for XCl (major) MH+=154 (m/z) and one for XBr (minor) MH+ 198 (m/z). This mixture gave the product in approximately 90% yield as the HBr salt.

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2007/105864; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6863-73-6, 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. 6863-73-6, name is 3-Chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

2-bromo-1,1-dimethoxyethane (3.7 g, 19.3 mmol) was added to a mixture of 48% hydrobromic acid and water (0.5 mL +5 mL) and refluxed for an hour. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated to get residue. This residue was dissolved in 1,2-dimethoxyethane, and added into a mixture of 3-chloropyrazin-2-amine (1 g, 7.7 mmol) and 48% Aq. HBr (0.15 mL) and refluxed for 3 h. The reaction mixture was cooled and the darksolid formed was filtered, washed with water and dried to get the titled compound. LC-MS:154.2 [M+H].

The chemical industry reduces the impact on the environment during synthesis 3-Chloropyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); A1;,
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. 6863-73-6, name is 3-Chloropyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H4ClN3

Sodium hydride (188.6 mg, 4.72 mmol) in N, N- dimethylformamide (3 mL) was slowly added dropwise at room temperature and benzyl alcohol was dissolved in it and it was stirred at room temperature for 1 hour. It was added dropwise slowly to a mixture of 2-amino-3-chloro-pyrazine and heating at 100 C refluxed for 15 hours. After cooling the reaction to room temperature and the solvent was evaporated under reduced pressure and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filter and concentrate under reduced pressure . By separation and purification of the residue by column chromatography (ethyl acetate / n-hexane = 1/4) to obtain the objective compound 300 mg at a yield of 53.76%.

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Institute of Science and Technology; Choo, Hyeon Ah; Bae, Ae Nim; Kim, Ji Yoon; Park, Pyong Gon; Lee, Ji Yeon; Noh, Eun Joo; Park, Jong Eun; Ra, Hyeon Hwa; (104 pag.)KR101481952; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6863-73-6,Some common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, molecular formula is C4H4ClN3, 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 1 3-Chloro-2-nitropyrazine STR11 Step A: S,S-Dimethyl-N-(3-chloropyrazin-2-yl)sulfilimine (2) To a mechanically stirred solution of 3.9 g (0.05 mol) dimethyl sulfoxide in 30 ml dry methylene chloride at -78 under nitrogen is added 13.1 g (0.046 mol) trifluoromethanesulfonic anhydride dropwise to afford a white precipitate. To this is added a solution of 5.0 g (0.039 mol) 2-amino-3-chloropyrazine (1) in 30 ml methylene chloride/15 ml dimethyl sulfoxide and the resulting solution is stirred at -78 for 2 hours and at -55 for 1 hour. The reaction mixture is then quenched with 50 ml of 5% aqueous sodium bicarbonate solution and stirred at -5 for 5 minutes. The reaction mixture is diluted with 200 ml methylene chloride and the phases are separated. The aqueous phase is extracted with 250 ml methylene chloride and the combined organic phases are washed with 3*75 ml portions of water and dried over anhydrous sodium sulfate. The solvent is removed from the rotary evaporator to give 5.8 g (79%) of 2 as yellow crystals, m.p. 106-108.

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

Reference:
Patent; Merck & Co., Inc.; US4709035; (1987); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem