Category: Pyrazines

Application of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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 4-(4-(oxetan-3-yl)piperazin-1-yl)aniline II (2.00 g, 8.57 mmoles), hunig’s base (3.29 mL) and 6,8-dibromoimidazo[1,2-a]pyrazine (2.37 g, 8.57 mmoles) was added in DMF (43 mL). The reaction was stirred at 85 C. in a pressure tube for overnight. The material was quenched with saturated sodium bicarbonate, extracted with DCM (120 mL*3) and the organic layers were combined and washed with water (120 mL*3), dried over anhydrous sodium carbonate and concentrated. The crude material was purified using a 120 g Isco column and eluted off using a stepwise gradient of 0-60% (10% MeOH/DCM). The desired fractions were combined and concentrated to provide the title compound III.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

4- (benzyloxycarbonyl) bicyclo [2.2.1] heptane-1-carboxylic acid (2g, 6.9mmol), HATU (2.89g, 7.6mmol),DIEA (3.56g, 27.6mmol) and (3-chloropyrazin-2-yl) methylamine hydrochloride (1.3g, 7.24mmol)The DMF (20 mL) solution was stirred at room temperature for 6 hours.Pour into water (100 mL) and extract with ethyl acetate (2 ¡Á 30 mL). The organic phase was washed with saturated aqueous NaCl solution.The organic phase was separated, dried over Na 2 SO 4, filtered and evaporated.Purified by column chromatography with ethyl acetate / petroleum ether = 1: 1 ~ 1: 0 to obtain 2g of the desired compound A-1, yield: 70%.

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Gentai Pharmaceutical Co., Ltd.; Chen Rongyao; (65 pag.)CN110964016; (2020); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

(i) A solution of bromine (0.11 ml) in chloroform (20 ml) was added dropwise over 20 minutes to a solution of 2-amino-5-methylpyrazine (0.218 g) in chloroform (30 ml) which was protected from light. The reaction mixture was stirred for 90 minutes after addition was complete and was then washed with water (50 ml). The organic phase was dried (MgSO4) and volatile material was removed by evaporation to give a yellow oil. The oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-3-bromo-5-methylpyrazine (0.286 g) as white solid, m.p. 51-52 C.; mass spectrum (positive chemical ionisation (+ve CI)): 188 (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; Zeneca Ltd.; US5668137; (1997); A;,
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. 19847-12-2, name is Pyrazinecarbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 19847-12-2

Example 8 Synthesis of the primary amine, pyrazin-2-ylmethanamine Raney nickel catalyst was carefully washed with THF and methanol making sure that the catalyst remained moist. The weight of the moist catalyst was 2.5 g after washing. This material was added to a solution of pyrazinecarbonitrile (17) (3.0 g) in 7N methanolic ammonia (120 mL). The mixture was shaken under a 50 p.s.i. atmosphere of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to provide the crude title compound. Purification was accomplished by conversion of the crude amine to the tert-butyl carbamate with excess di-tert-butyl dicarbonate in methylene chloride. Column chromatography (70:27:3 hexanes:ethyl acetate:methanol) provided 0.50 g of pure tert-butyl pyrazin-2-ylmethylcarbamate.

The synthetic route of 19847-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; US2008/119496; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 74290-67-8, 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. 74290-67-8 name is 2-Amino-5-bromo-3-methylpyrazine, 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.

EXAMPLE 11 Sodium hydride (60% dispersion in mineral oil; 0.1 g) was added portionwise to a stirred solution of 2-amino-5-bromo-3-methylpyrazine (0.188 g) in 1,2-dimethoxyethane (DHE; 4 ml). After 5 minutes 5-dimethylamino-1-naphthalenesulphonyl chloride (0.3 g) was added, in a single portion, and the reaction was allowed to a stir for 18 hours. 2M Aqueous citric acid solution (10 ml) was added and the reaction was extracted with dichloromethane (3*25 ml). The combined extracts were dried (MgSO4) and evaporated to give a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane/diethyl ether (1:1) to give 5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide as a cream solid (0.138 g, 33%), m.p. 171-172 C.; mass spectrum (+ve FAB, DMSO/methanol/NBA): 421 (M+H)+.

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

Reference:
Patent; Zeneca Limited; US5861401; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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. Computed Properties of C5H2ClN3

(3) Add 4.74 g (7.0 mmol) of 24-2 to a 100 mL three-necked flask.1.12 g (8.0 mmol) of 2-chloro-3-cyanopyrazine, 78.5 mg (0.35 mmol) of palladium acetate,290 mg (0.7 mmol) of X-Phos, 2.90 g of anhydrous potassium carbonate, and three times of deaeration with nitrogen.12 mL of DME and 6 mL of deionized water were injected, nitrogen was bubbled for 30 min, and heated at 100 C for 8 h.After the TCL monitoring reaction was completed, it was cooled to room temperature, extracted with 100 mL of dichloromethane and 200 mL of deionized water.The organic phase was washed three times with deionized water (100 mL ¡Á 3) and dried over anhydrous sodium sulfate for 10 min.After filtration and concentration, the crude product was passed through a silica gel column (5¡Á10 cm), and the pure product was separated and dried in vacuo.The product 24 (2TCzPZCN) was obtained in 2.32 g, yield 45%.

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

Reference:
Patent; Zhejiang Hongwu Technology Co., Ltd.; Ai Qi; Liu Junyuan; Duan Ke; Zhang Qisheng; (33 pag.)CN110256409; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313339-92-3, A common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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.

11482] 1 -Methyl-34(2R,3R)-2-methylpiperidin-3-yl)tet- rahydropyrimidin-2(1H)-one (404, 120 mg, 0.55 mmol) was dissolved in 10 mE DMF. To it were added 3,5-dichioropy- razine-2-cabonitrile (175 mg, 1.0 mmol) and DIEA (350 pL, 2.0 mmol). The mixture was stirred at RT for 30 mM, diluted with 150 mE EtOAc, washed with water x3, dried, concentrated in vacuo, and subjected to silica flash colunm using 0 to 3.5% MeOH in DCM to isolate 3-chloro-5-((2R,3R)-2-me- thyl-3-(3-methyl-2-oxotetrahydropyrimidin-i (2H)-yl)pip- eridin-i-yl)pyrazine-2-carbonitrile (405, 60mg, 31% yield).

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); 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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, A new synthetic method of this compound is introduced below., Recommanded Product: 4744-50-7

EXAMPLE 10; [] 5-(5,7-Dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-2-(oxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid; In a 4-ml scintillating vial, a solution of 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (148 mg, 0.5 mmol) in tetrahydrofuran (1.0 ml) was treated with a solution of pyrazine phthtalic acid anhydride (85 mg, 0.56 mmol) in tetrahydrofuran (1.0 ml) and N,N-dimethylformamide (0.5 ml). The reaction mixture was allowed to stir at room temperature for 1 hour. N,N-Diisopropylethylamine (220 mul, 0.13 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.6 mmol) were added. The reaction mixture was shaken vigorously for 10 seconds before being stirred at room temperature for 14 hours. The volatiles were evaporated invacuo and the residue purified by silica gel chromatography using a mixture of dichloromethane/ethyl acetate (3:1) as eluent. Pure fractions were collected and the solvent evaporated invacuo affording 25 mg (12 %) of the 2-amino-5-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.1H-NMR (300 MHz, CDCl3) delta 8.97 (s, 2H), 4.62-4.49 (m, 2H), 4.21-4.04 (m, 2H), 3.94 (dd, 1H, J = 14 Hz and J = 4 Hz), 2.91 (d, 1H, J = 17 Hz), 2.63 (dd, 1H, J = 17 Hz and J = 10 Hz), 1.68 (s, 9H).

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; NOVO NORDISK A/S; Ontogen Corporation; EP1214325; (2005); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 60187-00-0, 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. 60187-00-0, name is 3,5-Dimethylpyrazin-2-ol, This compound has unique chemical properties. The synthetic route is as follows.

2. 2-Iodo-3,5-dimethylpyrazine This was prepared from 2-hydroxy-3,5-dimethylpyrazine by the Procedure of Hirschberg and Spoerri, J. Org. Chem., 1961, 1907.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethylpyrazin-2-ol. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 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.

A 1000 mL single-neck round bottom flask was charged with 2-aminopyrazine (28.50 g, 300 mmol), N-iodosuccinimide(134.99 g, 600 mmol), methanol 340 ml,The mixture in the reaction flask was stirred at 80 C for 10 hours.TLC and GC confirmed the reaction was complete. After the reaction was completed, the solvent was removed by rotary evaporation to give a crude product, which was purified by silica gel column chromatography to give pure product2-Amino-5-iodopyrazine, after drying,Calculated yield 70.50%Purity 99.58% (HPLC).

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; Shandong Youbang Biochemical Technology Co., Ltd.; Geng Xuanping; Lai Chao; Lai Ziteng; Lai Xinsheng; (4 pag.)CN106674137; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem