Category: 56423-63-3

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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3BrN2

n-BuLi (25.4 ml_, 63.5 mmol, 2.5 M in hexane) was added drop wise to a -78 C solution of 2-bromopyrazine (10.1 g, 63.5 mmol) in toluene (150 ml_) under N2. After 10 min at -78 C, a solution of N-cyclobutylidene-2-methylpropane-2-sulfinamide (Preparation 50, 10.0 g, 57.71 mmol) in toluene (50 ml_) was added slowly. The resulting dark red solution was stirred for 1 hr at -78 C. The reaction was quenched by the addition of sat. NH4CI solution (10 ml_) and the reaction mixture dried (MgS04), filtered and concentrated in vacuo to give a brown oil. The crude product was purified by column chromatography on silica gel eluting with pet. Ether: EtOAc (100:0 to 0: 100) to MeOH: EtOAc (9:91 ) to afford the title compound as a yellow oil, 4.0 g, 27%. 1H NMR (400 MHz, CDCI3): delta 1 .21 (s, 9H), 1.86-1 .96 (m, 1 H), 2.08-2.19 (m, 1 H), 2.58-2.78 (m, 4H), 3.62-3.75 (br s, 1 H), 8.49 (d, 1 H), 8.56 (dd, 1 H), 8.80 (d, 1 H). LCMS m/z = 254 [M+H]+

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; CASIMIRO-GARCIA, Agustin; STROHBACH, Joseph Walter; HEPWORTH, David; LOVERING, Frank Eldridge; CHOI, Chulho; ALLAIS, Christophe Philippe; WRIGHT, Stephen Wayne; (213 pag.)WO2018/11681; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 56423-63-3, The chemical industry reduces the impact on the environment during synthesis 56423-63-3, name is 2-Bromopyrazine, I believe this compound will play a more active role in future production and life.

Methyl 4-(2-pyrazinyl) benzoate (0432) In a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were combined a solution of [4-(methoxycarbonyl)phenyl]boronic acid (1 g, 5.56 mmol, 1.20 equiv) in 1,4-dioxane (30 mL), 2-bromopyrazine (800 mg, 5.03 mmol, 1.00 equiv), a solution of Na2CO3 (1.5 g, 14.15 mmol, 3.00 equiv) in water (30 mL), and Pd(Ph3P)2Cl2 (330 mg, 0.47 mmol, 0.10 equiv). The resulting solution was stirred for 16 h at 90 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3¡Á30 mL of EtOAc, and the organic layers combined and concentrated under vacuum. This resulted in 0.8 g (74%) of the product as a white solid.

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

Reference:
Patent; Imago Biosciences, Inc.; Rienhoff, JR., Hugh Y.; McCall, John M.; Clare, Michael; Celatka, Cassandra; Tapper, Amy E.; (226 pag.)US2016/237043; (2016); 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, Computed Properties of C4H3BrN2

Preparation 133: 2-Chloro-4-(pyrazin-2-yl)aniline; [00303] To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.1 10g, 0.434 mmol), 2-bromopyrazine (0.090 g, 0.56 mmol), 1 ,1 ‘- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1 .06 mmol). The microwave vial was heated at 75C for 40 minutes under microwave irradiation. Further catalyst (0.012 g) was added and the vial was heated at 90C for 25 minutes under microwave irradiation. Further 2-bromopyrazine (0.060g), catalyst (12 mg) and 2M aqueous sodium carbonate (0.25 mL) were added and the reaction mixture was heated at 90C for an additional 30 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (2 x 15 mL), dried (Na2S04) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 7% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :10) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :5) (2×5 mL) and acetone (3 x 4 mL) to give the title compound as an off- white solid (0.039 g, 44%). 1 H-NMR (500 MHz, DMSO-d6) 5.86 (s, 2H), 6.89 (d, J = 8.5, 1 H), 7.85 (dd, J = 2.1 , 8.5 Hz, 1 H), 8.02 (d, J = 2.1 Hz, 1 H), 8.44 (d, J = 2.5 Hz, 1 H), 8.57 (dd, J = 1 .6, 2.5 Hz, 1 H), 9.12 (d, J = 1 .5 Hz, 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; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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 56423-63-3 as follows.

A mixture of ethyl 2-((diphenylmethylene)amino)acetate (6.0 g, 22.47 mmol), 2-bromopyrazine (7.1 g, 44.90 mmol), potassium carbonate (9.30 g, 67.40 mmol) and tetrabutyl ammonium iodide (8.10 g, 22.40 mmol) in N-methyl-2-pyrrolidone (25 mL) was heated in a sealed tube at 110 C. for 16 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3¡Á50 mL). The organic layers were washed with brine (25 mL) and dried over sodium sulfate. Removal of solvent under vacuum afforded crude product which was purified in Combi-Flash instrument using a gradient of methanol in chloroform. Yield: 4.90 g (63%). 1H NMR (300 MHz, DMSO-d6) delta: 1.16 (t, 3H), 4.07 (q, 2H), 5.26 (s, 1H), 7.18 (dd, 2H), 7.38-7.61 (m, 8H), 8.56 (d, 1H), 8.57 (d, 1H), 8.60 (s, 1H). MS (ES) MH+: 346.3 for C21H19N3O2.

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; BASARAB, Gregory Steven; GOWRAVARAM, Madhusudhan Reddy; HAUCK, Sheila Irene; ZHOU, Fei; US2014/206677; (2014); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 56423-63-3

Example 117BPreparation of Compound (142b)(142b)[00659] To a solution of compound (142a) (1.00 g, 2.27 mmol) in dioxane (30 mL) was added K2C03 (1.57 g, 11.4 mmol, 5 equiv.), Pd(PPh3)2Cl2 (30 mg, 3%) and 2-bromopyrazine (720 mg, 4.45 mmol, 2 equiv.). The mixture was degassed within an ultrasonic cleaner for 1 hr. Under argon protection, the reaction mixture was stirred at 90 C for 4 hr. The mixture was cooled to room temperature. The solvents were evaporated under reduced pressure. The residue was purified through FCC to give 460 mg of compound (142b). Characteristic analytical data: 1H NMR 8.67 (1H), 8.46 (1H), 8.32 (1H), 6.47 (1H, vinyl), 5.39 (1H), 4.54-4.62 (m, 1H, AcOCH).

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; CHU, Daniel; WANG, Bing; YE, Tao; WO2012/83112; (2012); A2;,
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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromopyrazine

Crystals of 2 were obtained by the slow-diffusion method between 3 layers: 1st layer is a solution of Fe(OTs)2*6H2O(0.096 g, 0.2 mmol, 1 equiv.) and NH4SCN (0.030 g, 0.4 mmol, 1 equiv.) in a water/methanol mixture (1/1, 10 ml); 2nd one is a water/methanol mixture (1/1, 10 ml); 3rd one is a solution of 2-bromopyrazine (0.127 g, 0.8 mmol, 1 equiv.) in methanol (3 ml). After 2 weeks red plates grew in the second layer; they were collected, washed with water and dried in air. Yield is 0.050 g (50%). Anal. Calc. for Fe1C18H16O2N10S2Br4: C, 25.59; H, 1.90; N, 16.58; S,7.58. Found: C, 24.91; H, 1.77; N, 16.42; S, 7.67%. Principal IR absorption bands for 2 (cm-1): 2080 (s), 1510 (m), 1456 (m),1381 (s), 1130 (s), 1057 (m), 1056 (m), 1020 (s).

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shylin; Gural Skiy; Bykov; Demeshko; Dechert; Meyer; Hauka; Fritsky; Polyhedron; vol. 87; (2015); p. 147 – 155;,
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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., Product Details of 56423-63-3

To a reaction flask were added compound 28 (100 mg, 0.189 mmol), 2-bromopyrazine (50 mg, 0.27 mmol), Pd(dppf)Cl2 (5 mg, 0.006 mmol) and sodium carbonate (60 mg, 0.558 mmol), 5 mL glycol dimethyl ether and 0.9 mL water were added, bubbled with nitrogen gas for 10 minutes, and the reaction was heated to 100 C in microwave and reacted for half an hour. After TLC detected the reaction was complete, the reaction was concentrated, purified by silica gel column chromatography to afford 41 mg of a product, yield: 45.3%. LC-MS(APCI): m/z = 480.3 (M+1)+. 1H NMR (400 MHz, CDCl3) delta 8.68 (s, 2H), 8.58 (s, 1H), 8.52 (s, 1H), 8.30 (s, 1H), 8.03 (s, 1H), 7.68 (d, J = 8.9 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 4.91 (d, J = 50.6 Hz, 1H), 4.35 (s, 1H), 3.68 (dd, J = 36.4, 23.2 Hz, 2H), 3.37 – 3.28 (m, 1H), 3.15 (d, J = 12.4 Hz, 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; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 56423-63-3,Some common heterocyclic compound, 56423-63-3, name is 2-Bromopyrazine, molecular formula is C4H3BrN2, 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.

General procedure: A mixture of the respective pyrimidine halide derivative (II) (0.15 mmol), the respective boronic acid derivative (III) (0.18 mmol), and K2003 2M (0.3 mL, 0.6 mmol) in ethanol (3 mL) is purged with argon, tetrakis5 (triphenylphosphine)-palladium (0.0075 mmol) is added, and the RM is heated at 9000 overnight. Alternatively, thereaction can be performed in a microwave apparatus, at 120C for 15- 30 mm. The RM is filtered through a 0.45 um Glass MicroFiber filter, washed with EtOH/MeCN and DMF. The filtrate is purified either by preparative HPLC or FC. Alternatively, it is diluted with water, if needed the pH is adjusted, and extracted with EtOAc (3x). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure. The residue is purified by preparative HPLC or by FC. The title compound is prepared according to the general procedure A described above, using N-(2-(6-fluoro-4- methoxy-2-methyl-i H-indol-i -yl)ethyl)-6-(4-(4,4,5,5-tetramethyl-i ,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-4-amine and 4-chloro-6-methoxypyrimidine. LC-MS E: tR= 1.10 mm; [M+H]+ =484.88.

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; FRETZ, Heinz; LYOTHIER, Isabelle; POTHIER, Julien; RICHARD-BILDSTEIN, Sylvia; SIFFERLEN, Thierry; WYDER PETERS, Lorenza; POZZI, Davide; CORMINBOEUF, Olivier; (306 pag.)WO2017/85198; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 56423-63-3, The chemical industry reduces the impact on the environment during synthesis 56423-63-3, name is 2-Bromopyrazine, I believe this compound will play a more active role in future production and life.

A sealed microwave vial containing (9R, 135)- 13 -[4-(2-amino-5 -chlorophenyl)-6-oxo- 1 ,6-dihydropyrimidin- 1 -yl]-3 ,9-dimethyl-3 ,4,7, 15 -tetraazatricyclo [12.3.1.026]octadeca- 1(1 8),2(6),4, 14,1 6-pentaen-8-one hydrochloride (0.01 g, 0.017 mmol), prepareddescribed in Example 313, 2-bromopyrazine (5.51 mg, 0.035 mmol) and EtOH (1 ml)was heated in a microwave at 150 C for 30 mm, cooled to rt, and concentrated. To the residue were added Cs2CO3 (0.030 g, 0.093 mmol), Pd(OAc)2 (1.05 mg, 4.66 jimol),Xantphos (5.39 mg, 9.31 jimol), and 2-bromopyrazine (5.51 mg, 0.035 mmol), followeddioxane (0.93 1 ml). The reaction mixture was degassed with Ar for 10 mm. The vial was sealed and heated at 85 C. After 4 h, the reaction was cooled to rt and concentrated. Purification by reverse phase chromatography afforded (9R, 135)-i 3-(4- {5-chloro-2-[(pyrazin-2-yl)amino]phenyl} -6-oxo- 1 ,6-dihydropyrimidin- 1 -yl)-3 ,9-dimethyl-3 ,4,7, 15-tetraazatricyclo[ 12.3.1 .02?6]octadeca- 1(1 8),2(6),4, 14,1 6-pentaen-8-one trifluoroacetate(2.95 mg, 20% yield) as a yellow solid. MS(ESI) m/z: 582.5 (M+H). ?H NMR(400MHz, CD3OD) oe 9.09 (s, 1H), 8.73 (d, J=5.i Hz, 1H), 8.23 – 8.19 (m, 2H), 8.08 (dd,J=2.8, 1.4 Hz, 1H), 7.89 (d, J=2.6 Hz, 1H), 7.73 (s, 1H), 7.67 (d, J2.6 Hz, 1H), 7.53 (dd,J=5.i, 1.5 Hz, 1H), 7.50 (s, 1H), 7.43 (dd, J8.9, 2.5 Hz, 1H), 6.77 (s, 1H), 6.02 (dd,J=12.7, 4.3 Hz, 1H), 4.05 (s, 3H), 2.76 – 2.67 (m, 1H), 2.43 – 2.32 (m, 1H), 2.15 – 2.01 (m, 2H), 1.68 – 1.44 (m, 2H), 1.02 (d, J=6.8 Hz, 3H), 0.81 – 0.65 (m, 1H). Analytical HPLC (Method A): RT = 7.06 mm, 94.0% purity; Factor XIa Ki = 560 nM.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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. 56423-63-3 name is 2-Bromopyrazine, 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.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-chloro-5-[[4-methyl-6-(methylarnino)pyrimidin-2-yl]amino]benzarnide (100 mg, 0.34 mmol, 1.00 equiv), Xantphos (8 mg, 0.07 mmol, 0.20 equiv), Pd2(dba)3 (7 mg, 0.03 mmol, 0.10 equiv), Cs2C03 (200 mg, 0.68 mmol, 2.00 equiv), DMSO (5 raL), 2-bromopyrazine (55 mg, 0.35 mmol, 1 .00 equiv). The resulting solution was stirred for 8 h at 80 C in an oil bath . The solids were fi ltered out. The crude product was purified by Prep-HPLC with the following conditions (2-AnalyseHPLC-SHIMADZU(HPLC-10)): Column, XB ridge Shield RP 18 OBD Column, 30* 150mm,5um; mobile phase, Wateri 1 OMMOL/L NH4HC03) and ACN (25.0% ACN up to 45.0% in 7 min); Detector, UV 254220nm. This resulted in 15.2 mg (12%) of the title compound as a white solid.

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; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; MILLS, James Edward John; MUNCHHOF, Michael John; (202 pag.)WO2019/79485; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem