Category: Pyrazines

5049-61-6, 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 5049-61-6 as follows.

3,5-Dibromo-2-aminopyrazine N-Bromosuccinimide (5.1 g, 28.7 mmol) was added slowly and portion wise to a mixture of aminopyrazine (1.3 g, 13.6 mmol) in dimethylsulfoxide (11 ml) and water (17 ml). During the addition of N-bromosuccinimide, the temperature of the reaction mixture was maintained below 15 C. After the addition, the reaction mixture was stirred for 16 h at RT. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 10 % Na2C03 solution followed by washing with water and brine. The organic layer was collected, dried over sodium sulfate and concentrated in vacuo to obtain crude product. The product was purified using column chromatography. Yield: 1.51 g 1H NMR (CDC13): 5.04 (2H, s), 8.03 (1H, s)

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41270-66-0, 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, A new synthetic method of this compound is introduced below.

2-chloro-5,6-diphenylpyrazine (10 gm), 4-(isopropylamino)-1 -butanol (44 gm) and N-methylpyrrolidine (50 mL) were charged into a 250 mL round bottom flask at 30C. The reaction mass was heated to 190C and stirred for 10 hours. The reaction mass was cooled to 30C and poured into cold water, extracted with ethylacetate, dried over anhydrous magnesium sulphate and then concentrated to get 9 gm of the title compound.

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. REDDY’S LABORATORIES LIMITED; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAHANUKAR, Vilas Hareshwar; CHINTADA, Krishnarao; SHAIKH, Latif Jafar; YARRAGUNTLA, Sesha Reddy; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; (33 pag.)WO2017/29594; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41270-66-0, 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. 41270-66-0 name is 5-Chloro-2,3-diphenylpyrazine, 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.

6 g of the compound of the formula (1), 7 g of isopropylamine and 5 mL of dimethyl sulfoxide were placed in a sealed pressure-resistant reaction vessel, and the mixture was heated to 90 C for 48 hours, and the reaction was completed. The reaction solution was cooled to 25 C, then 18 mL of ethanol was added, and the solution was dissolved at 80 C, then 24 mL of water was added dropwise over 1 h, a large amount of solid was precipitated, and the temperature was lowered to 25 C, stirred for 0.5 hour, and suction-filtered to obtain a solid.Drying at 80 C for 24 h under vacuum gave 6 g of the compound of formula (2) as a pale yellow solid.The yield was 92.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2,3-diphenylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Dongguan Dongyangguang Pharmaceutical Research And Development Co., Ltd.; Liu Yongjun; Wang Zhongqing; Liao Shouzhu; Luo Zhonghua; (5 pag.)CN109422698; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-74-7, 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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To an oven-dried microwave vial was added ethyl 2-amino-1,3-oxazole-5-carboxylate (546 mg, 3.50 mmol), Cs2CO3 (2279 mg, 6.99 mmol), Pd2(dba)3 (80 mg, 0.09 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and the vial was capped and purged with nitrogen. 2,4-Dichloropyridine (0.378 mL, 3.50 mmol) was added via syringe, followed by 1,4-dioxane (18 mL) (degassed) and the reaction mixture was heated to 160 C for 1 h under microwave irradiation. CH2Cl2 (40 mL) was added to the crude reaction mixture together with silica (5 g). The solvents were removed under reduced pressure and the crude product was purified by flash silica chromatography with CH2Cl2 (containing 1% methanolic ammonia) as eluent.The resulting brown solid was triturated with Et2O to give ethyl 2-(4-chloropyridin-2-ylamino)oxazole-5-carboxylate (626 mg, 67%) as a pale yellow solid, which was collected by filtration and dried under vacuum.

The synthetic route of 6-Chloropyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Noonan, Gary M.; Dishington, Allan P.; Pink, Jennifer; Campbell, Andrew D.; Tetrahedron Letters; vol. 53; 24; (2012); p. 3038 – 3043;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

98-97-5, A common compound: 98-97-5, name is Pyrazine-2-carboxylic acid, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Under Argon, a stirred solution of carboxylic acid (0.37 mmol,1.0 eq.) and Et3N (0.48 mmol, 1.3 eq.) in dry THF (7 mL) was cooledto 10 C. Ethyl chloroformate (0.55 mmol, 1.5 eq.) was drop wiseadded and the resulting mixture was stirred for 2 h. Afterwards, asolution of sodium azide (0.63 mmol, 1.7 eq.) in water (2 mL) wasadded in one portion. After 1 h at 10 C, the reactionwas found tobe complete (TLC) and was quenched into iced water (5 mL). Themixture was extracted with EtOAc (3 10 mL) and the combinedorganic layers were successively dried over MgSO4, filtered andevaporated. The crude acyl azide was placed in dry toluene (20 mL)and heated at reflux for 1 h to give the corresponding crude isocyanate.The latter was placed in dry dioxane (7 mL) prior to addingthe appropriate amine 8, 9 or 10 (0.37 mmol, 1.0 eq.). The solutionwas heated at 100 C for 24 h. The reaction mixture was cooled andthe volatiles were removed to dryness in vacuum at 40 C.

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

Reference:
Article; Boulahjar, Rajaa; Ouach, Aziz; Bourg, Stephane; Bonnet, Pascal; Lozach, Olivier; Meijer, Laurent; Guguen-Guillouzo, Christiane; Le Guevel, Remy; Lazar, Said; Akssira, Mohamed; Troin, Yves; Guillaumet, Gerald; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 274 – 287;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, 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 4858-85-9 as follows.

A 12L 3-neck round bottom flask fitted with a magnetic stirrer under nitrogen was charged with zinc dust (745 g, pre-activated, 11.4 mol, 2 eq.) and DMA (2 L, anhydrous). 1, 2-dibromoethane (71 mL, 0.855 mol, 0.15 eq, Aldrich) was then added over 10 minutes, followed by TMSC1 (108 mL, 0.855 mol, 0.15 eq, Acros) over 20 minutes. The reaction mixture was stirred for 25 minutes at room temperature. A solution of N-Boc-3-iodoazetidine (2420 g, 8.55 mol, 1.5 eq, CNH Technologies) in DMA (5 L, anhydrous) was added via a 2L addition funnel over 2 h keeping the internal temperature below 65 C using a water bath. The suspension was stirred for 1 hour at RT at which point it was degassed with nitrogen. Stirring was stopped and the suspension was allowed to stand. A 22L 3-neck round bottom flask fitted with a mechanical stirrer was charged with 2, 3-dichloropyrazine (850 g, 5.70 mol, 1.0 eq, AK Scientific), PdCl2dppf-CH2Cl2 (140 g, 171 mmol, 0.03 eq, Aldrich), Cul (67.3 g, 353 mmol, 0.062 eq, Aldrich), and DMA (5 L, anhydrous). The solution was degassed with nitrogen. The clear zinc reagent solution above the residual solid zinc was poured into the 22L flask under nitrogen. The brown solution was degassed with nitrogen and heated to 80 C for 16 hours at which point LCMS indicated complete conversion of 2, 3-dichloropyrazine. The reaction mixture was transferred to brine (8 L) in 50L separatory funnel. Water (8 L) and EtOAc (15 L) were added and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 10 L). The combined organics were washed with water (3 x 10 L) and brine (5 L), dried over sodium sulfate and evaporated. The resulting residue was purified by column chromatography (eluting with hexanes/ethyl acetate = 10: 1) to get 536 g of pure tert-butyl 3-(3-chloropyrazin-2- yl)azetidine- 1 -carboxylate and 121 g of mixed fractions. The impure material was distilled under high vacuum to remove the impurity (N-Boc-azetidine) to give 81 g of pure tert-butyl 3- (3-chloropyrazin-2-yl)azetidine- 1 -carboxylate.Total: 617g, Yield: 40%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4858-85-9, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of amine 1 (1.0 mmol) in dry DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil, 2.2 mmol) and alkyl iodide (4.0 mmol). The resulting mixture was stirred under nitrogen at room temperature for 25 minutes. The reaction mixture was then quenched with water (6 mL), extracted with diethyl ether (2¡Á12 mL) and the combined organics were washed with brine, dried over sodium sulfate and concentrated. Biorg. Med. Chem. 2001, 9, 1149-1154.; Prepared from 2-amino-3,5-dibromopyrazine and iodomethane (568 mg, 4.00 mmol) according to general procedure 1. Purification by column chromatography (12 g ISCO column eluding with hexanes and ethyl acetate; gradient 100% hexanes to 70% hexanes) provided the substituted aminopyrazine (171 mg, 61%) as a yellow oil; 1H NMR (300 MHz, CDCl3) delta 8.11 (s, 1H), 3.07 (s, 6H).

The synthetic route of 2-Amino-3,5-dibromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alcon, Inc.; US2006/142307; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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 1458-01-1, 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) and NaOH (6 mol/l in water; 240 mL; 1.44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60¡ãC. Yield: 99.6 g (107percent of theory) C5H5ClN4O2 ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [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, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; FRATTINI, Sara; HAMPRECHT, Dieter; KLEY, Joerg; WO2013/64450; (2013); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 36070-80-1

Preparation of Starting Material 5-chloro-N,N-dimethylpyrazine-2-carboxamide (SM-1) 5-chloropyrazine-2-carboxylic acid (1.00 gram, 6.31 mmol) in dichloromethane (30 ml) was treated with catalytic amount of dimethylformamide, followed by (COCl)2 (0.85 ml, 9.46 mmol). The resulting mixture was stirred over night. The reaction was concentrated in vacuo, and dried under vacuum to give desired 5-chloropyrazine-2-carbonyl chloride as solid (1.05 g, 100%).

The synthetic route of 36070-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2010/234285; (2010); 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. 5049-61-6, name is Pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., 5049-61-6

To a stirred solution of pyrazin-2-amine (2.00 g, 21 .0 mmol) in CHCI3 (25 mL) was added NCS (3.65 g, 27.3 mmol) portionwise and the reaction mixture was stirred at room temperature for 6h. Progress of reaction was monitored by TLC. After completion, the reaction mixture was poured in to ice cold H20 (20 mL) and extracted with EtOAc (2 c 40 mL). The organic layer was separated, washed with brine (25 mL), dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by combi flash chromatography (20% EtOAc in hexane) to afford 3,5-dichloropyrazin-2-amine X-10a (1 .50 g) as an off-white solid. Yield: 37%. (0851) 1H NMR (400 MHz, DMSO-cfe) d 7.02 (brs, 2H), 8.06 (s, 1 H).

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:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem