Category: 33332-28-4

Related Products of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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.

[0504] Compound 481A was prepared by an analogous method as that of 473B, except using compound 2-chloro-6-aminopyrazine in place of compound 2-bromo-6-aminopyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-28-4, name is 2-Amino-6-chloropyrazine, 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. Recommanded Product: 2-Amino-6-chloropyrazine

Example 1C 6-(3-butenyloxy)-2-pyrazinamine A suspension of NaH (60percent, 618 mg, 15.45 mmol) in dioxane (30 mL) at 0° C. was treated with 3-buten-1-ol (1.33 mL, 15.45 mmol), stirred for 2 hours, treated with 2-amino-6-chloropyrazine (1 g, 7.72 mmol), stirred at 100° C. for 2.5 days, cooled to room temperature, and diluted with ethyl acetate. The mixture was washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography eluding with hexanes/ethyl acetate (2:1) to provide the desired product (390 mg, 31percent). MS (DCI/NH3) m/z 166.12 (M+H)+; 1H NMR (500 MHz, benzene-d6) delta 2.66 (m, 2H), 4.42 (t, J=6.87 Hz, 2H), 5.24 (dd, J=10.22, 1.98 Hz, 1H), 5.30 (m, 1H), 6.04 (m, 1H), 7.64 (s, 1H), 7.65 (s, 1H).

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lin, Nan-Horng; Li, Gaoquan; Przytulinska, Magdalenna K.; Sowin, Thomas J.; Sullivan, Gerard M.; Tao, Zhi-Fu; Tong, Yunsong; Wang, Le; US2005/215556; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-amino-6-chloropyrazine (5 g, 38.60 mmol) in a mixture of anhydrous chloroform (120 mL), anhydrous acetonitrile (12 mL) and anhydrous methanol (12 mL) was addedslowly, at 0CC, NBS (7.56 g, 42.45 mmol, 1.1 eq.) and the mixture was warmed to room temper-ature and continuously stirred for 1 h. The excess solvent was removed in vacuo and the obtained crude material (light brown solid) was purified by column chromatography (Hexane/DCM/MeOH = 50/50/0 then 0/1 00/0 then 0/95/5) to afford 5-bromo-6-chloropyrazin-2-amine(6.34 g, 30.42 mmol, 79percent) as white crystals. ESI-MS: 209.90 [M+H]+. 1 H NMR (300 MHz,CDCI3) 6 7.69 (s, 1 H), 4.78 (br s, 2H).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-chloropyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-6-chloropyrazine

EXAMPLE 3 N-(6-Chloro-pyrazin-2-yl)-2,6-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 2.0 g (7 mmols) of methyl 2,6-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 1.1 g (8.4 mmols) of 2-amino-6-chloro-pyrazine were reacted in 150 ml of xylene analogous to Example 2, and the reaction product was isolated and recrystallized from ethylene chloride. 2.1 g (79percent of theory) of N-(6-chloro-pyrazin-2-yl)-2,6-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained. Melting point: 296°-298° C. 1H-NMR (CDCl3 +d-TFA): delta=9.55 (s, 1,3′-H); 8.55 (s, 1,5′-H); 8.05-7.55 (m, 3,5-H, 7-H, 8-H); 3.00 (s,3,N-CH3); 2.60 (s,3,CH3).

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; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-28-4, name is 2-Amino-6-chloropyrazine, 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 33332-28-4, Application In Synthesis of 2-Amino-6-chloropyrazine

A solution of 6-chloropyrazin-2-amine (10.0 g, 77 mmol) in DMSO (100 ml) was treated with 1-iodopyrrolidine-2,5-dione (20.84 g, 93 mmol). The reaction mixture was stirred at RT for 2 days and then added to water (800 ml). The pH was adjusted to pH 8-9 using a sat. NaHCO3 solution and the resulting suspension was filtered, washing with water (*3) and dried under vacuum to afford the titled compound as an orange solid; LC-MS Rt=0.83 mins; [MeCN+H]+ 296.0, Method 2 minLowpH.

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-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; Adcock, Claire; Leblanc, Catherine; US2013/184282; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-28-4, 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. 33332-28-4 name is 2-Amino-6-chloropyrazine, 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.

Following a literature procedure (Walters, I.A.S. Tetrahedron Lett. 2006, 47, 341), a solution of dimethylzinc (2.0 M in toluene, 75.0 mL, 150.0 mmol) was carefully added in 25 mL portions to a solution of 2-amino-6-chloropyrazine (10.0 g, 77.0 mmol) and l ,3-bis(diphenylphosphino)propane-nickel (II) chloride (4.2 g, 7.8 mmol) were dry in dioxane (400 mL) under a nitrogen atmosphere. The reaction was stirred at rt for 2 h and then heated to 50 0C for 1 h and 95 0C overnight. The reaction was allowed to cool to rt and an additional charge of dimethylzinc was added (22 mL, 44 mmol) and the reaction was then maintained at 95 0C overnight. The reaction was cooled to rt, quenched over 15 min with MeOH and then concentrated to a brown solid. Water and EtOAc were added to the solid, and the mixture was sonicated. The solid was removed by filtration and brine was added to the EtO Ac-water mixture. The layers were separated, and the organic layer was dried (Na2SO^, and concentrated to give 9.72 g (~70 purity) of 6-methylpyrazin-2-amine, which was carried forward without further purification: LCMS (m/z): 110.0 (MH+), R = 0.21 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-chloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2009/115572; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-28-4, name is 2-Amino-6-chloropyrazine, 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 33332-28-4, Recommanded Product: 33332-28-4

2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous NH3 (28percent, 10 ml.) and heated to 100°C in a sealed tube for 18 hours. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave 6- chloropyrazin-2-amine as a white solid (2.28 g, 17.6 mmol, 91 percent yield). 1H NMR (d6-DMSO, 400 MHz) ? 6.9 (brs, 2H), 7.70 (d, J = 0.4, 1 H), 7.80 (d, J = 0.4, 1 H); LC-MS (ZQ, 6 minutes) Rt = 1.05 minutes; m/z (ESI+) 130 (M+H).6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in CH2CI2 (60 ml.) at 0°C.A/-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0°C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25percent EtOAc-hexanes, gave 5-bromo-6-chloropyrazin-2-amine as a yellow solid (1 .69 g, 8.16 mmol, 42percent yield). 1H NMR (de-DMSO, 400 MHz) ? 7.1 (brs, 2H), 7.65 (s, 1 H); LC-MS (ZQ, 4 minutes) Rt = 1.46 minutes; m/z (ESI-) 205 (M-H).A mixture of 5-bromo-6-chloropyrazin-2-amine (1 .00 g, 4.8 mmol), copper (I) iodide (914 mg, 4.8 mmol), 18-crown-6 (95 mg, 0.36 mmol) andtetrakis(triphenylphosphine)palladium (0) (83 mg, 0.072 mmol) was suspended in dry DMF (20 ml.) and a stream of nitrogen was passed through for 5 minutes. Potassium cyanide (312 mg, 4.8 mmol) was added and the mixture was stirred at room temperature for 30 minutes, then refluxed at 200°C for 3 hours. The mixture was cooled, diluted with EtOAc and absorbed onto silica gel (10 g). DMF was removed by evaporation. The product was purified by flash chromatography, eluting with 1 :1 EtOAc-hexanes, to yield 5- amino-3-chloropyrazine-2-carbonitrile as a yellow solid (607 mg, 3.93 mmol, 82percent yield). 1H NMR (d6 DMSO, 400 MHz) ? 7.87 (s, 1 H), 8.1 (brs, 2H); LC-MS (ZQ, 4 minutes) Rt = 1.20 minutes; m/z (ESI-) 153 (M-H).

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-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; COLLINS, Ian; LAINCHBURY, Michael; MATTHEWS, Thomas Peter; READER, John Charles; WO2013/68755; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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.

Step-1: Synthesis of 6-chloro-5-iodopyrazin-2-amine To a stirred solution of 2-amino-6-chloropyrazine (2.0 g, 1.0 eq., 15.50 mmol) in acetonitrile (20 mL) was added NIS (3.46 g, 1.0 eq., 15.50 mmol) at 0 C. The reaction was allowed to stir at RT. Progress of the reaction was monitored by TLC and LCMS After completion of the reaction the solvent was evaporated under vacuum and the solid was extracted using ethyl acetate (3*100 mL). The combined organic layers were washed (brine), dried (anhydrous Na2SO4) and concentrated under vacuum to get the solid which was purified by normal phase column chromatography to get the desired product (1.7 g, 42%).

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; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-6-chloropyrazine

A solution of 2-amino-6-chloropyrazine (25g, 193.1 mmol) in MeOH (500 ml_) was treated with NBS (34.3 g, 193.1 mmol), portion-wise, over 1 hour. The resulting mixture was stirred for 16 hours thereafter. TLC analysis at this time shows a small amount of starting material remaining. Another 1.4 g NBS added and reaction heated to 50 0C for 2 hours. The mixture15 was then cooled to 38 0C and treated with NCS (25.8 g, 193.1 mmol). The reaction mixture was heated to 500C for 16 hours thereafter. The mixture was then cooled to room temperature and treated with water (500 ml_). The precipitate was collected by filtration and dried in a vacuum dessicator to afford 45.4 g (97% yield) of 2-amino-5-bromo-3,6- dichloropyrazine as a white solid: 13C NMR (75 MHz, CDCI3) delta 149.9 (s), 145.6 (s), 129.6 (s),20 121.5 (S). LCMS (15-95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 4.51 min on 30 mm column, (M+H)+ = 244, (M+H+ACN)* = 285.

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; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-28-4, name is 2-Amino-6-chloropyrazine, 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. Application In Synthesis of 2-Amino-6-chloropyrazine

To a mixture of MeOH (6 mL) in DMSO (12 mL) was added slowly NaH (1.2 g of 60% in oil, 30 mmol) and stirred at room temperature for 30 min. 2-amino-6-chloropyrazine (1.29 g, 10 mmol) was added to the mixture portionwise and heated at 80 C for 2 h. The reaction mixture was cooled, water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified bycolumn chromatography to give 2-amino-6-methoxypyrazine (888 mg, 71%) as a slightly yellow solid. 1H NMR (200 MHz, CDCl3) delta 7.60 (s, 1H), 7.55 (s, 1H), 4.44 (br, 2H), 3.90 (s, 3H); 2-amino-6-methoxyprazine (186 mg, 1.45 mmol) was dissolved in MeOH. To the solution was added N-bromo-succinimide (568 mg, 3.19 mmol) and stirred at room temperature for 30 min. The reaction mixture was concentrated via vacuo, ethyl acetate was added and washed with water. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give a product 1e (242 mg, 59%). 1H NMR (200 MHz, CDCl3) delta4.91 (br, 2H), 3.96 (s, 3H);

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwak, Se Hun; Lee, Gee-Hyung; Gong, Young-Dae; Bulletin of the Korean Chemical Society; vol. 33; 12; (2012); p. 4271 – 4274;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem