Category: 33332-29-5

Some common heterocyclic compound, 33332-29-5, name is 2-Amino-5-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. HPLC of Formula: C4H4ClN3

General procedure: To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150C in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH:DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-29-5, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, Name is 2-Amino-5-chloropyrazine, 33332-29-5, 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.

Step A: S,S-Dimethyl-N-(5-chloropyrazin-2-yl)sulfilimine (5) Compound 5 is prepared from 2-amino-5-chloropyrazine as described above for 2 in Example 1A to afford pure 5 as a smelly, tan solid, m.p. 119-120.

Statistics shows that 2-Amino-5-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 33332-29-5.

Reference:
Patent; Merck & Co., Inc.; US4609659; (1986); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

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

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
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 33332-29-5 as follows. COA of Formula: C4H4ClN3

(iii) 2-Amino-5-chloropyrazine (1.7 g) was dissolved in chloroform (190 ml) and pyridine (1.3 ml) was added under an argon atmosphere. The flask and its contents were protected from light and a solution of bromine (0.7 ml) in chloroform (85 ml) was added over a period of 1 hour. After stirring for 2 hours more bromine (0.07 ml) in chloroform (8.5 ml) was added and, after stirring for 30 minutes, pyridine (0.2 ml) was added. The reaction mixture was stirred for a further 30 minutes then washed with water (50 ml) and the organic phase was separated. The solvent was removed by evaporation and the residue was purified by chromatography through a bed of silica (90 g), eluding with hexane (200 ml) followed by dichloromethane. Dichloromethane fractions containing the product were evaporated to give 2-amino-3-bromo-5-chloropyrazine (1.68 g); 1 H NMR (d6 DMSO): 6.94 (br s, 2H), 8.09 (s, 1H); mass spectrum (+ve CI): 208 (M+H)+.

According to the analysis of related databases, 33332-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Ltd.; US5668137; (1997); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-29-5, 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. 33332-29-5 name is 2-Amino-5-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.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-5-chloropyrazine, and friends who are interested can also refer to it.

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

Example 776-chloro-2-[3-nitro-4-(trifluoromethyl)phenyllimidazo[1 ,2-alpyrazineA solution of 5-chloropyrazin-2-amine (0.336 g, 2.6 mmol) and 2-bromo-1 -[3-nitro-4- (trifluoromethyl)phenyl]ethanone (0.81 1 g, 2.6 mmol) in acetonitrile (15 mL) is stirred at 100 C for 18 hr. The mixture is concentrated to give the title compound (890 mg), which is used without further purification. LCMS m/z = 343.3 [M+H]+, fR = 2.65 min.

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

Reference:
Patent; PAMLICO PHARMACEUTICAL INC.; ATKINSON, Robert N.; OMMEN, Andy J.; VEAL, James M.; HUANG, Kenneth H.; SMITH, Emilie, D.; WO2012/88411; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 33332-29-5, name is 2-Amino-5-chloropyrazine, 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. Application In Synthesis of 2-Amino-5-chloropyrazine

General procedure: Sodium nitrite (3.4 g, 50 mmol, 1.3 eq.) was added in small portionsto 98% sulfuric acid (15 mL) ice bath, and the mixture was allowed towarm up and heated to 60. When getting clear, the solution wascooled in an ice bath again. A solution of 2-amino-pyrazine (9) (4 g,39.3 mmol, 1 eq.) in 98% sulfuric acid (15 mL) was added dropwise.The reaction mixture was stirred at 40 for 1 h. After cooling to roomtemperature, it was slowly poured onto crushed ice and stirred until nonitrogen run out. The solution was adjusted to pH 6 with a 40% solutionof sodium hydroxide, resulting in lots of sodium sulfate which wasfiltered off whereafter. The filtrate was extracted with EA (50 mL×3),and the combined organics were dried (Na2SO4), filtered and concentratedin vacuo to give the product as a white precipitate (6.38 g,53%).

The synthetic route of 2-Amino-5-chloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Shuang; Xu, Mingshuo; Guo, Qi; Zhu, Fuqiang; Jiang, Xiangrui; Xie, Yuanchao; Shen, Jingshan; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 748 – 759;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

To a solution of 5-chloropyrazin-2-amine (500 mg, 3.86 mmol) in DCM (5mL) was added NBS (686.92 mg, 3.86 mmol), and the brown mixture was stirred at 40 C for 1 hour. After cooling to r.t., the mixture was filtered through silica gel and eluted with EtOAc (20 mL x 3), and the filtrate was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 20% to 40% to 50%) to give the product (600 mg) as a solid. *H NMR (400MHz, CDC13 ) _ = 7.98 (s, 1H), 5.05 (br s, 2H).

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

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (364 pag.)WO2018/98499; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-29-5, 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.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

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

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-29-5, name is 2-Amino-5-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. Recommanded Product: 2-Amino-5-chloropyrazine

1 , 1 -Dimethylethyl (5-chloro-2-pyrazinyl)carbamateTo a 500 mL flask was added THF (83 mL), 5-chloropyrazin-2-amine (10 g, 77 mmol) and Boc20 (19.71 mL, 85 mmol). The dark solution was heated to reflux for 48 h, then cooled to RT, concentrated, and the residue purified via silica gel chromatography on the ISCO RF (liquid load, 330 g column, 0-10% EtOAc/Hexane over 30 min). Concentration of fractions containing product afforded 1 ,1-dimethylethyl (5-chloro-2-pyrazinyl)carbamate as a slightly yellow oil. This was used without further purification. Approximately 5 g of starting material was recovered. The rest of the material was a mixture of products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-29-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem