Month: December 2020

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. 4774-14-5, name is 2,6-Dichloropyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 4774-14-5

Aniline (265.7 mg, 2.85 mmol) and 2,6-dichloropyrazine (427.2 mg, 2.87 mmol) were dissolve in n-butanol (2.0 mL), and 4.0 M hydrochloric acid in 1,4-dioxane (2 mL) was added. The mixture was heated to 120 C for 96 h, poured in water (30 mL), extracted with ethyl acetate (30 mL), the organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL) and brine (25 mL), concentrated and purified by chromatography (30 g silica gel, 0.5-1.0% ethyl acetate-dichloromethane) to afford 6-chloro-N-phenylpyrazin-2-amine (225.9 mg, 38% yield) as a dark yellow semi-solid; 1H NMR (400 MHz, CDCl3): delta 8.10 (s, 1H), 7.97 (s, 1H), 7.40-7.35 (m, 4H), 7.17-7.12 (m, 1H), 6.74 (s, 1H); Calcd mass for C10H8ClN4: 205.04; LRMS (ESI) m/z [M+H]+ = 206.20.

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:
Article; Kashyap, Sudhir; Sandler, Joel; Peters, Ulf; Martinez, Eduardo J.; Kapoor, Tarun M.; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2253 – 2260;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, Product Details of 19745-07-4

N-ethyl piperidin-4-ol(200 mg1.55 mmol) was added to dry THF (10 mL) and the mixture was cooled to 0oC, then NaH (60percent, 124 mg3.1 mmol) was added slowly. The mixture was stirred at 0oC for 0.5 h and then 2,5-dichloropyrodazine(231 mg1.55 mmol) was added and stirred overnight. The reaction was quenched with iced water and extracted with DCM, the organic layer was washed with brine, dried and concentrated to afford compound 12(330 mg, white solid).LC-MS: 242.1(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, 2,5-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fu, Yan; Tang, Shuai; Su, Yi; Lan, Xiaojing; Ye, Yan; Zha, Chuantao; Li, Lei; Cao, Jianhua; Chen, Yi; Jiang, Lei; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5332 – 5336;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 3-AMINO-2-PYRAZINE-CARBOXYLATE (10 g, 65.3 mmol) was dissolved in glacial acetic acid (50 mL) by warming to approximately 45oC. To the warm solution was added bromine (3-7 MOL) in acetic acid (5 mL) dropwise and the resulting mixture was stirred at room temperature for 20 minutes. The solution was diluted with water (300 ML) and then stirred at room temperature for 30 minutes, which resulted in a precipitate. The precipitate was then filtered, washed with water and dried to afford methyl 3-AMINO-6-BROMO-2-PYRAZINE-CARBOXYLATE as a yellow solid (14. 2 g, 94 percent). IH NMR (300 MHz, CDC13) 63. 99 (s, 3 H), 8.30 (s, 1 H) ; 13C NMR (100 MHZ, CDC13) A 53.02, 123.49, 124.85, 150.24, 154.70, 166.04.

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

Reference:
Patent; BIOGEN IDEC MA INC.; WO2004/92177; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 681249-57-0, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, molecular formula is C6H7F3N4, 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. SDS of cas: 681249-57-0

To the CH2Cl2 solution of 4-(4-(bromomethyl)benzyloxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (0.13 g, 0.284 mmol) was added 2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (0.060 g, 0.313 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.152 ml, 0.853 mmol). The mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and CH2Cl2 (10 mL) and extracted. The organic layer was concentrated and the resulted oil was purified on silica gel column eluted with MeOH and CH2Cl2 to give 2-(2,6-dioxo-piperidin-3-yl)-4-[4-(2-trifluoromethyl-5,6,8,8a-tetrahydro-1H-[1,2,4]triazolo[1,5-a]pyrazin-7-ylmethyl)-benzyloxy]-isoindole-1,3-dione as a white solid (120 mg, 74%). Melting point: 128-130 C. LC-MS m/e=569. HPLC Waters Symmetry C-18, 3.9¡Á150 mm, 5 micro, 1 mL/min, 240 nm, isocratic 50/50 CH3CN/0.1% H3PO4 in H2O=3.64 min (99%); 1H NMR (DMSO-d6) delta 1.94-2.12 (m, 1H, CHH), 2.41-2.47 (m, 1H, CHH), 2.54-2.67 (m, 1H, CHH), 2.77-2.95 (m, 1H, CHH), 3.01 (t, J=5.4 Hz, 2H, CH2), 3.81 (d, J=7.6 Hz, 4H, CH2, CH2), 4.24 (t, J=5.1 Hz, 2H, CH2), 5.09 (dd, J=5.4, 12.7 Hz, 1H, NCH), 5.37 (s, 2H, CH2), 7.37-7.55 (m, 5H, Ar), 7.61 (d, J=8.5 Hz, 1H, Ar), 7.76-7.88 (m, 1H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) delta 21.95, 30.90, 46.54, 47.67, 48.73, 49.21, 59.42, 69.89, 115.53, 116.59, 120.21, 127.42, 128.95, 133.26, 135.25, 136.99, 137.06, 152.84, 155.50, 165.29, 166.75, 169.87, 172.71. Anal Calcd for C27H23F3N6O5+0.5 H2O+0.2 Et2O: C, 56.37%; H, 4.42%; N, 14.19%; Found C, 56.27%; H, 4.20%; N, 14.05%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 681249-57-0, its application will become more common.

Reference:
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, 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 56423-63-3, Recommanded Product: 56423-63-3

Under nitrogen protection conditions,(S) -2- amino-3-phenylpropanoic acid (1.6 g, 9.5 mmol), 2-bromopyrazine (1 g, 6.3 mmol) were added sequentially to 50 mL of dry N, N- dimethylacetamide, Potassium carbonate (1.7 g, 12.6 mmol) and cuprous iodide (0.2 g, 0.9 mmol) were added and the temperature was raised to 90 C with stirring.After 48 hours the TLC test showed the reaction was complete and the reaction was allowed to cool to room temperature. 30 mL of ethyl acetate and 10 mL of water were added and the temperature was lowered to 0 C. The pH was adjusted to 3 with 6 M HCl solution. The organic phase was separated and the aqueous phaseThe organic phase was combined, dried over anhydrous sodium sulfate and filtered after drying. The residue was purified by column chromatography on a rotary evaporator (petroleum ether: ethyl acetate = 1: 1) Product 0.7g, yield 46%.

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

Reference:
Patent; Fudan University; Shao Liming; Xu Yulong; Chen Yiyi; Li Wei; Xie Qiong; (25 pag.)CN107151254; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4744-50-7, A common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.

Example-1; Preparation of 3-(5-chloropyridin-2-yI)-carbamoylpyrazine-2-carboxylic acid2-Amino-5-chloro pyridine (171.2 g) was suspended in 800 ml toluene and mixture was heated to 48-52 C. Pyrazine-2,3-dicarboxylic acid anhydride (100 g) was added to the suspension at same temperature. The resulting reaction mixture was stirred for 2 hrs at 48-52 C. The reaction slurry was cooled to 20-25 C and stirred for 30 min. The solid was filtered and washed with 100 ml toluene. The filtered solid was added to a mixture of 1000 ml water and 100 ml cone. HCl at 10-15C. The solid was stirred for 60 min at 10-15 C and filtered. The solid was slurred in 400 ml water, filtered and washed with 100 ml water.The solid was dried at 60-70 C to yield 17O g of title compound.

The synthetic route of 4744-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MATRIX LABORATORIES LTD; WO2008/126105; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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 A Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml). The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97%) of 4-(2-pyrazinyl)benzaldehyde.

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

Reference:
Patent; Zhu, Bin; Marinelli, Brett; Macielag, Mark J.; US2005/250713; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 75907-74-3, 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. 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

In the reaction flask, 2-hydroxymethyl-3,5,6-trimethylpyrazine (3 g, 0.02 mol) was added, Dissolved in 20 mL of dichloromethane, The ice bath was added dropwise with stirring Thionyl chloride (3 mL, 0.04 mol), Stirring reaction 1.5h TLC monitoring to the reaction is complete, The solvent and the remaining dichlorosulfoxide were evaporated under reduced pressure to give a pale yellow mass 2-chloromethyl-3,5,6-trimethylpyrazine 3.2 g, 20 mL of DMF (N, N-dimethylformamide) was added.

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, (3,5,6-Trimethylpyrazin-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KPC Pharmaceuticals, Inc; song, LI MING; Bai, Fei; Yang, ZHAO XIANG; (15 pag.)CN104341358; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Hydrazine hydrate (23.59 mL, 480.75 mmol) was added dropwise to a stirred mixture of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 g, 418.04 mmol) in EtOH (2 L). The mixture was heated at 50 C. under nitrogen. The resulting thick suspension was stirred at 50 C. for 16 hours. Further hydrazine (2.5 mL) was added in one portion and the suspension was stirred at 50 C. for a further 24 hours. Ethanol (500 mL) was charged to the thick reaction mixture and the mixture was allowed to cool to room temperature. The resulting suspension was filtered and the solid washed with ethanol (1 L) and dried in vacuo to give 3-amino-6-bromopyrazine-2-carbohydrazide (98 g, quantitative) as a cream solid: 1H NMR Spectrum; (DMSO-d6) 4.52 (2H, s), 7.59 (2H, s), 8.30 (1H, s), 9.74 (1H, s); Mass Spectrum [M+H]+=232.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-6-bromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; BARLAAM, Bernard Christophe; DELOUVRIE, Benedicte; OUVRY, Gilles; LAMBERT-VAN DER BREMPT, Christine Marie, Paul,; HARRIS, Craig Steven; BERRY, David; TOMKINSON, Gary Peter; REID, Gary Patrick; US2014/206700; (2014); 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine, A new synthetic method of this compound is introduced below., category: Pyrazines

2-dimethylamino-5-bromo-pyrazine (21) (1.37g, 6.8mmol) was dissolved in dehydrated tetrahydrofuran (THF) (50ml), it was under an argon atmosphere. The solution was cooled to -80 C. with acetone bath, 1.57 M n-butyl lithium (n-BuLi) slowly added hexane solution (10.8 ml), and stirred for 1 hour. Then it was slowly added N, N-dimethylformamide (DMF) (2.0ml, 26mmol) to this mixed solution was stirred for 1 h allowed to warm to room temperature. Then stirred for 15 minutes Water was added to the reaction mixture and extracted with ethyl acetate (2 ¡Á 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [silica gel 46.9g; hexane – ethyl acetate (1: 1)] and purified by, 5-aldehyde-2-dimethyl-amino-pyrazine (22) (975mg, 6.5mmol, 95 %) as a light yellow powder solid.

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; UNIVERSITY OF ELECTRO-COMMUNICATIONS; MAKI, SHOJIRO; NIWA, HARUKI; (25 pag.)JP2015/193584; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem