Tag: M.W=100-200

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. 59489-32-6, name is 5-Chloro-2,3-dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Chloro-2,3-dimethylpyrazine

To a degassed solution of 1,1-dimethylethyl (lR,4S,6R)-4-[(E/Z)-2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)ethenyl]-3-azabicyclo[4.1.0]heptane-3-carboxylate D6 (150 mg) and 5-chloro-2,3-dimethylpyrazine D56 (73.5 mg) in 1,2- DME (3 ml) sodium carbonate 2M (1 ml, 2.000 mmol), dichloropalladium – triphenylphosphane (1 :2) (30.1 mg, 0.043 mmol) was added and the mixture was heated to 90C for 1.5 hours. The mixture was cooled down to room temperature, then diluted with EtOAc and washed with water and brine. Organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. Crude was purified by flash chromatography on silica gel (Cy to Cy/EtOAc 1 : 1) affording the title compound D57 (26.6 mg).UPLC (IPQC): rt = 1.18 minutes peak observed: 330 (M+l) Ci9H27N302 requires 329.

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 59489-32-6.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5780-66-5, A common heterocyclic compound, 5780-66-5, name is Pyrazine-2-carbaldehyde, molecular formula is C5H4N2O, 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 5 Synthesis of the compound represented by the following formula; [Show Image] The compound A (50 mg) and 2-pyrazinecarboxyaldehyde (200 mg) were dissolved in methanol (10 ml) and then 100 mul of acetic acid was added thereto, followed by stirring at 80°C for 3 hours. After the reaction solution was neutralized with triethylamine, it was filled on a Sephadex LH-20 column chromatography and developed with methanol. The desired fraction was concentrated and dried to give a hydrazone compound (45 mg). The resulting hydrazone compound (20 mg) was dissolved in methanol-tetrahydrofuran (1:1) (10 ml) and then NaBH3CN (20 mg) and 10percent HCl-MeOH (3 ml) were added thereto, followed by stirring for 60 minutes. After the reaction solution was concentrated, a small amount of triethylamine was added to the residue and the mixture was filled on a Sephadex LH-20 column chromatography and developed with methanol. The desired fraction was concentrated and dried to give the compound represented by the above formula (6.0 mg) as a red solid. FAB (m/z): 627 (M + H)+ 1H-NMR (300 MHz, DMSO-d6, delta ppm): 11.23 (1H, s), 9.03 (1H, d, J = 1.2 Hz), 8.82 (1H, d, J = 8.7 Hz), 8.74 (1H, d, J = 8.4 Hz), 8.51 (1H, d, J = 2.7 Hz), 8.46 (1H, dd, J = 1.2 Hz, 2.7 Hz), 7.19 (1H, d, J = 1.8 Hz), 7.03 (1H, d, J = 1.8 Hz), 6.83 (1H, dd, J = 1.8 Hz, 8.7 Hz), 6.80 (1H, dd, J = 1.8 Hz, 8.4 Hz), 6.43 (1H, t, J = 4.5 Hz), 6.18 (1H, br), 5.96 (1H, d, J = 8.4 Hz), 5.05 (1H, br), 4.43 (2H, d, J = 4.5 Hz), 4.05 (1H, m), 3.92 (2H, m), 3.77 (1H, m).

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; BANYU PHARMACEUTICAL CO., LTD.; EP1666485; (2006); 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 16298-03-6

To a solution of methyl 3-amino- pyrazine-2- carboxylate (5.00 g, 32.7 mmol) in 1,2-dimethoxyethane (80 mL) were added ?2 (4.14 g, 16.3 mmol), copper(I) iodide (1.87 g, 9.80 mmol) and cesium iodide (8.48 g, 32.7 mmol) undernitrogen. Then isoamyl nitrite (13.2 mL, 98.0 mmol) was added dropwise at 20 C. The reaction was stirred at 75 C for 2 h, then quenched with water (100 mL). The aqueous layer was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by silica gel chromagraphy eluting withPE/EtOAc (5i02, PE: EtOAc = 1: O1O:1, v/v) to give the title compound. MS (ESI) mlz:264.7 [M+Hj ?H NMR (400MHz, DMSO-d6) oe = 8.71 (d, J=2.2 Hz, 1H), 8.63 (d, J2.0Hz, 1H), 3.93 (s, 3H)

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MILLER, Michael; CHOBANIAN, Harry, R.; HE, Shuwen; HAO, Jinsong; PIO, Barbara; GUO, Yan; XIAO, Dong; (213 pag.)WO2018/118670; (2018); 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 939412-86-9

The reaction mixture of 2- (5-chloro-4-fluoro-2-isopropoxy-3- (6- (trifluoromethyl) pyridin-3-yl) phenyl) propanoic acid (520 mg, 1.28 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (293 mg, 2.05 mmol) , Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (998 mg, 1.92 mmol) and N, N-Diisopropylethylamine (330 mg, 2.56 mmol) in DMF (20 mL) was stirred at room temperature for overnight. After completed, the solvent was evaporated in vacuo and the residue was dissolved with ethyl acetate. The mixture was washed with water and brine, dried over Na 2SO 4, filtered and evaporated in vacuo to give the product which was used directly for the next step without further purification. MS (M+H) + 531.1.

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; BEIGENE, LTD.; LI, Jing; ZHAO, Haibo; WANG, Zhiwei; (193 pag.)WO2018/103688; (2018); 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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3-chloropyrazine-2-carboxylate

Step 2: Methyl 3-(pyridin-2-yl)pyrazine-2-carboxylate (Y2) To a solution of the product from step 1 (100 mg, 0.58 mmol) in toluene (2 mL) was added Pd(PPh3)4 (134 mg, 0.12 mmol) and 2-(tributylstannyl)pyridine (213 mg, 0.58 mmol) at room temperature and the resulting mixture was heated to 100 C overnight. After cooled to RT, the mixture was filtered and 5 mL of aq. KF solution was added to the filtrate. The resulting mixture was stirred for 30 mins and extracted with EtOAc (5 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography (30% EtOAc in petroleum ether) to provide the title compound. LRMS m/z (M+H) 216.1 found, 216.1 required.

The synthetic route of 27825-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); 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. 1458-03-3, name is Methyl 3-amino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H6ClN3O2

(b) Methyl 2-amino-5-chloropyrazine-3-carboxylate (3.75 g) was added to a solution of sodium hydroxide (2.0 g) in water (20 ml) and the solution was heated under reflux for 1.5 hours. The reaction mixture was cooled to 0 C. and the precipitate which had formed was collected by filtration. The solid was redissolved in water (60 ml) with heating and the solution was filtered. The filtrate was then acidified to pH 2 with 2M hydrochloric acid. The precipitate which formed was collected by filtration and washed with ice/water (2*20 ml) and dried under vacuum. The solid was suspended in diphenyl ether (15 ml) and heated at reflux under an argon atmosphere for 15 minutes. The reaction mixture was cooled to ambient temperature and diluted with hexane (15 ml). The precipitate which formed was collected by filtration and washed with hexane (3*25 ml) to give 2-amino-5-chloropyrazine (1.78 g); 1 H NMR (d6 -DMSO): 6.55 (br s, 2 H), 7.67 (d, 1 H), 7.95 (d, 1 H); mass spectrum (+ve CI): 130 (M+H)+.

According to the analysis of related databases, 1458-03-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; US5866568; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

2,3-Dichloro-pyrazine (1.48 g, 0.01 mol),and Ethynyl-benzene (1.53 g, 0.015 mol) was added in a lOOmL flask which contained 30mL of Et3N with stirring, and then the catalyst of Cul(0.38 g, 0.002 mol)and Pd(PPh3) 2C12(2 g, 0.002 mol) was added into the mixture. The reaction mixture was warmed to 80C for 0.5h, lc-ms indicated 2,3-Dichloro-pyrazine was consumed. The reaction mixture was cooled to room temperature. Filtrated, the filtrate was concentrated to give the crude product, the crude product was further purified by flash chromatography to afford 2-Chloro-3-phenylethynyl-pyrazine. (1.5 g, yield: 71%). LC/MS (ESI+): 215 [M+l]+ 217 [ +3]+

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-25-1, 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. 33332-25-1 name is Methyl 5-chloropyrazine-2-carboxylate, 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.

To a mixture of methyl 5-chloropyrazine-2-carboxylate (1 g, 5.79 mmol) and 2,2,2-trifluoroethanol (2.111 ml, 29.0 mmol) was added potassium carbonate (0.801 g, 5.79 mmol). The reaction was stirred at ambient temperature for 16 hrs. The reaction was partitioned between ethyl acetate and water. The organic portion was concentrated and purified in 10-60% EtOAc/Heptane to give the title compound (1.1 g, 4.66 mmol, 80%). MS m/z=237.1 (M+H).

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

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25911-65-3, 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. 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 4 Synthesis of 3-Amino-6-bromopyrazine-2-carbonitrile (Intermediate 3) To a solution of intermediate 2 (1.7 g, 14 mmol) in acetic acid (40 mL) at RT was added bromine (0.95 mL, 19 mmol) slowly. The resulting mixture was heated at 60 C. for 30 min and then cooled to RT. The mixture was poured into ice water and the resulting solid filtered. After thoroughly washed with water, the title compound was obtained as a yellow solid (2.3 g, 83%). 1H NMR (500 MHz, DMSO-d6): delta 8.44 (s, 1H), 7.60 (br s, 2H). MS (ES+): m/z 199 (M+H)+.

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

Reference:
Patent; TargeGen, Inc.; US2007/259876; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4774-15-6, 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. 4774-15-6, name is 2,6-Dimethoxypyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

the molar ratio of Sodiummethoxide and dibromopyrazine is 5:1 placed into three-necked flask with astirrer and a thermometer, added 500ml of Distilled water, start the mixer andwith speed of 200r / min it was stirredfor 10min; After the mixing the mixture was placed at reflux apparatus , heatedup to 60 C, refluxed for 2h, , the collected reflux liquid was put into abeaker then placed in an ice-water bath , at 4 C under ice the precipitatewas allowed to stand for 2h, filtered toobtain precipitate and spare after rotary evaporation drying; The massconcentration of concentrated sulfuric acid is 98% and after drying as mentioned above the precipitatemass ratio is 12: 1 were mixed andtogether poured into a beaker of 500mL, after stirred with a glass rod for10min placed on the shaker and Oscillating reaction for 2 h ,then againadded 50mL of nitric acid solution with a mass concentration of 95% , continues to oscillate the reaction for 20minto obtain a mixed solution; The ratio of the mixed liquid and ammonia water is1:5, the ammonia water was poured into the above mentioned mixed solution, placedthe reaction solution on a magnetic stirrer, with speed of 600r / min it was stirred for 10s , afterwards reduce speed to200r / min and continue to stir for 30min. After completion of the stirring,400ml of anhydrous ethanol added into the mixture solution, placed intoultrasonic vibration device, ultrasonic vibration reaction for 1h, thentransferred to a distillation apparatus, heated to 60 C, ethanol was removedby distillation,for drying used vacuum freeze-drying machine and after crushingof solid particles; Take 1g of the above mentioned solid particles and put into100ml of beaker , added 15ml of glacial acetic acid and 10ml of hydrogenperoxide with a mass concentration of 30%, water bath warmed to 40 C, andafter the 6hrs of reaction filtrated to obtain precipitate and dried to obtain 2,6-diamino-3,5-dinitro-1-oxidepyrazine.

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, 2,6-Dimethoxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Changzhou University; CHEN, Xing-quan; (5 pag.)CN105399690; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem