Month: July 2021

Synthetic Route of 123-32-0, 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. 123-32-0, name is 2,5-Dimethylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 3,6-dimethyl-2- (4-isopropyl) benzoyl pyrazine, comprising the steps of: (1) 2,5-dimethyl pyrazine take 0.2mmol, 4- benzoyl-carboxylic acid isopropyl 0.4mmol, 0.02 mmol silver phosphate, potassium persulfate 5mL reaction tube was placed 0.4mmol, 1.4mL was added di methylene chloride, 0.6 mL of distilled water was added, and the mixture was placed in an oil bath at 40 heated, reaction 24h, cooled to room temperature to obtain a reaction solution;(2) The step (1) the resulting reaction mixture was directly concentrated to give a concentrate, the concentrate with ethyl acetate / petroleum ether = 1/2 (v / v) as the developing solvent, separation by thin layer chromatography to give 20 mg desired product in 40% yield.

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

Reference:
Patent; Henan Agricultural University; Wu Zhiyong; Zhao Mingqin; Li Yuan; (10 pag.)CN108101856; (2018); A;,
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. 59303-10-5, name is 2-Chloro-5-methylpyrazine, A new synthetic method of this compound is introduced below., Product Details of 59303-10-5

Example 1.18: Preparation of 2-(4-(((lr,4r)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)-5-methylpyrazine (Compound 9).; A mixture of 4-(((l r,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (36.1 mg, 0.089 mmol), prepared in Example 1.17, Step A, 2-chloro-5-methylpyrazine (25 mg, 0.194 mmol), and triethylamine (50 muEpsilon, 0.359 mmol) in iPrOH (2 mL) was heated under microwave at 150 C for 1 h, at 200 C for 1 h, and then at 180 C for 14 h. The mixture was purified by HPLC (5- 95% CH3CN). Fractions containing the title compound were partly concentrated and the residue was extracted with 1M NaOH and CH2C12 (three times). The combined organic phases were dried over MgS04, filtered, and concentrated to give the title compound (24.1 mg, 0.052 mmol, 58.7 % yield) as a white solid. Exact mass calculated for C24H32FN3O3S: 461.21 , found: LCMS m/z = 462.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.24-1.58 (m, 6H), 1.81-1.96 (m, 5H), 2.17-2.20 (m, 2H), 2.40 (s, 3H), 2.84-2.95 (m, 3H), 3.05 (s, 3H), 3.25-3.31 (m, 1H), 3.37 (d, = 6.2 Hz, 2H), 4.25-4.28 (m, 2H), 7.40-7.43 (m, 1H), 7.58-7.60 (m, 1H), 7.66-7.68 (m, 1H), 7.95 (s, 1H), 8.06 (s, 1H).

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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

Dimethylzinc (lOOmL of a 2M solution in toluene) was added dropwise over 0.5h to astirred solution of 6-chloro-2-pyrazinamine (12.9g) and [1,3-fe(diphenylphosphmo)propane]nickel(n) chloride (5.4g) in dioxane (200mL) under anitrogen atmosphere. The reaction mixture was heated at reflux for 18h, then cooled toroom temperature and quenched cautiously with zso-propanol (30mL) and methanol(50mL). After removal of solvent in vacua, the residue was partitioned betweendichloromethane and aqueous ammonium chloride. The organic phase was filtered throughcelite, dried (MgSO4), filtered and evaporated to give the crude product as an orange solid.Chromatography on silica gel eluting with ethyl acetate/methanol mixtures gave the sub- title compound (5.1g). Used directly.

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

Reference:
Patent; ASTRAZENECA AB; WO2004/108692; (2004); A1;,
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 14508-49-7 as follows. Safety of 2-Chloropyrazine

General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; vol. 423; 1; (2014); p. 11 – 15;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

22047-25-2, name is Acetylpyrazine, 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 Acetylpyrazine

Step 1 Preparation of 4,4-difluoro-1-(2-pyrazinyl)butane-1,3-dione Ethyl difluoroacetate (2.23 g, 18 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (10 mL). To the stirred solution was added 25% sodium methoxide (4.68 g, 22 mmol) followed by acetylpyrazine (2.00 g,16 mmol). After two hours stirring at room temperature, a precipitate formed and THF (10 mL) was added to the reaction. The reaction was stirred an additional 25.9 hours, then treated with 3N HCl (10 mL). The organic layer was collected, washed with brine (20 mL), dried over MgSO4, and concentrated in vacuo and recrystallized from methylene chloride/iso-octane to give the diketone as a brown solid (2.23 g, 68%); mp 103-110 C.; 1 H NMR (CDCl3) 300 MHZ 14.00 (br s, 1H), 9.31 (d, J=1.4 Hz, 1H), 8.76 (d, J=2.4 Hz, 1H), 8.68 (dd, J=1.4 Hz 2.4 Hz, 1H), 7.20 (s, 1H), 6.03 (t, J=54.0 Hz, 1H); 19 F NMR (CDCl3) 300 MHz: -127.16 (d); M+200.

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5756529; (1998); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23688-89-3, 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 23688-89-3 as follows.

4-Phenoxyaniline (0.185 g, 1.0 mmol), 6-chloropyrazine-2-carboxylic acid (0.158 g, 1.0 mmol) and 30 mL of dichloromethane were added to the reaction flask, and Et3N (0.202 g, 2.0 mmol) was added. Then, EDCI (0.287 mg, 1.5 mmol), HOBt (0.20 g, 1.5 mmol) was added, and the reaction was carried out at 25 C for 2.0 hours. The reaction was completed by TLC, and the reaction was completed. The reaction mixture was washed twice with water and once with saturated brine.The organic phase is dried over anhydrous sodium sulfate and de-solued to give a crude product.The ethanol was recrystallized to give a white solid, m.p. 160-162 C, yield: 83.0%

According to the analysis of related databases, 23688-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chen Lei; (6 pag.)CN108997228; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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 297172-19-1, Computed Properties of C6H9N3

EXAMPLE 3 5-[5,6-Dihydroimidazo[1,5-a]pyrazin-7(8H)-yl]-3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazoline Prepared from 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine as described for Example 1, step c (0.033 g, 37%). deltaH (360 MHz; CDCl3) 4.07 (2H, dd, J=6 and 6), 4.44 (2H, dd, J=6 and 6), 4.92 (2H, s), 6.93 (1H, s), 7.22-7.32 (2H, m), 7.37-7.41 (1H, m), 7.60 (1H, s), 7.69 (1H, dd, J=8 and 8), 7.96 (1H, dd, J=8 and 8), 8.05-8.09 (2H, m), 8.73 (1H, d, J=8); m/z (ES+) 386 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Chambers, Mark Stuart; Collins, Ian James; Goodacre, Simon Charles; Hallett, David James; Jones, Philip; Keown, Linda Elizabeth; Maxey, Robert James; Street, Leslie Joseph; US2003/45532; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 33332-28-4, name is 2-Amino-6-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. Recommanded Product: 2-Amino-6-chloropyrazine

A solution of 6-chloropyrazin-2-amine (2 g, 15.44 mmol) and N BS (13.7 g, 77 mmol) in CHCI3 (100 ml) was heated at reflux for 20 hours. The resulting mixture was purified bychromatography on silica eluting with DCM. The relevant fractions were concentrated in vacuo and the crude product was dissolved in EtOAc (~100 ml), washed with 10 percent sodium thiosulfate (2 x 100 ml), brine, dried (MgS04) and were concentrated in vacuo to afford the title compound; 1 H NMR (400 MHz, CDCI3) delta 5.4-5.0 (2H, br s).

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

Reference:
Patent; NOVARTIS AG; CHARLTON, Steven, John; LEBLANC, Catherine; MCKEOWN, Stephen, Carl; WO2012/7539; (2012); 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Add [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.445 g, 0.596 5 mmol) to the suspensions ofmethyl1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)phenyl]cyclo propanecarboxylate (2.00 g, 5.4 mmol,), sodium carbonate (1.26 g, 11.9 mmol) and 2,5-dichloropyrazine (8.93 mmol) in 1,4-dioxane (20 mL) and water (4 mL) under N2. Then the reaction mixture is stirred at 100 oc for 3 h under N2. The reaction mixture is concentrated to give a black solid. The mixture is diluted with water (20 mL) and 10 extracted with EtOAc (30 mL x 3). The combined organic layers are washed with brine (20 mL), dried over anhydrous Na2S04, filtered and evaporated to afford the crude product. The crude product is purified by flash chromatography eluting with petroleum ether: EtOAc (1 :2) to afford title compound (1.0 g 57.6percent) as a yellow solid, LCMS (m/z): 288.9 [M+Ht. 1H NMR (400 MHz, CD3Cl) 8 = 8.80 (d, J = 1.2 Hz, 1H), 8.65 (d, J = 1.2 Hz, 1H), 7.96 (d, J 15 = 8.4 Hz, 2H), 7.51 (d, J= 8.4 Hz, 2H), 3.67 (s, 3H), 1.72- 1.66 (m, 2H), 1.28- 1.23 (m, 2H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19745-07-4.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; MA, Tianwei; WU, Liang; ZHANG, Xuejun; (109 pag.)WO2019/41340; (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. 41270-62-6, name is 2-Chloro-6-phenylpyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-6-phenylpyrazine

2-Chloro-6-phenylpyrazine (108 mg, 0.56 mmol), tert-butyl 3-amino-5- methyl-lH-pyrazole-1-carboxylate (142 mg, 0.72 mmol), palladium(II) acetate (15 mg, 0.07 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (65 mg, 0.1 mmol), potassium carbonate (820 mg, 5.9 mmol), and dioxane (4 mL) were combined and the mixture degassed with nitrogen for 2 minutes before heating to 90C for one hour. The reaction was partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate (3x), organics were combined, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography (10-65% ethyl acetate in hexanes) to give the title compound as a white solid (92 mg, 0.26 mmol, 46% yield); MS (ESI) MS (ESI) m/z 352.4 [M+l]+.

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; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem