Category: 76537-18-3

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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Bromo-5-chloropyrazin-2-amine

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol), triethylamine (290 mg, 2.88mmol), cuprous iodide (5 mg, 0.33 mmol) and palladium(II)bis(triphenylphosphine) dichloride(13 mg, 0.02 mmol) were dissolved in tetrahydrofuran (5 mL). The mixture was stirred at rt, thentrimethylsilylacetylene (0.15 mL, 1.06 mmol) was added dropwise to the mixture. After theaddition, the reaction mixture was warmed to 55 oc and stirred for 1 h. The reaction mixture wascooled to rt, and diluted with ethyl acetate (50 mL). The mixture was filtered. The filtrate wasconcentrated in vacuo, and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 3011) to give the title compound as a light yellow solid (208 mg, 96 %).MS (ESI, pos. ion) m/z: 227.00 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.98 (s, 1H), 5.11 (s, 2H), 0.31 (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; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, A common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol),Triethylamine (290 mg, 2.88 mmol), cuprous iodide(5mg, 0.33mmol)And bis(triphenylphosphine)palladium dichloride (13 mg, 0.02 mmol) was dissolved in tetrahydrofuran (5 mL).The reaction solution was stirred at room temperature.Then trimethylethynyl silicon (0.15 mL, 1.06 mmol)Slowly adding dropwise to the above reaction solution,After completion of the dropwise addition, the resulting reaction solution was heated to 55 C to continue the reaction for 1 hour.After the reaction system is cooled to room temperature,The reaction solution was diluted with ethyl acetate (50 mL).Filter and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (PE/EA (v/v) = 30/1).The title compound was obtained as a pale yellow solid ( 208 g, 96%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate C75-Chloro-3-( I ,3-dimethyl-I H-pyrazol-4-yl)-pyrazi n-2-ylam me To a solution of 3-bromo-5-chloropyrazin-2-amine (3.75 g, 18.01 mmol) in DME (90 mL) wasadded 1 ,3-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (4 g, 18.01 mmol), bis(triphenylphosphine)palladium(ll) chloride (0.632 g, 0.901 mmol) and Na2003 (aq.2.OM) (27.0 mL, 54.0 mmol). The reaction was heated to 90C overnight. The reaction was added to water (250m1) and the product was extracted into EtOAc (2 x 230m1). The organic phase was washed with brine, dried over MgSO4. The solids were removed by filtration, washed with EtOAc and the filtrate concentrated under vacuum. The crude product was purified by flash column chromatography, eluting with 0-10% gradient of (2M NH3 in MeOH)in DCM on a 80g Si-column, loading with DCM to give the product (2.5g)LCMS: Rt 0.81 mins; MS mlz 224.0 [M+H]+; Method 2minLowpHvol

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

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3,Some common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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 a degassed solution of 3-bromo-5-chloro-pyrazin-2-amine, la, (20.80 g, 99.79 mmol), Et3N (41.74 mL, 299.4 mmol), iodocopper (0.6 g, 2.99 mmol) and dichloropalladium; triphenylphosphine (1.40 g, 2.00 mmol) in THF (388 mL) was added ethynyl-trimethyl-silane (14.10 mL, 99.79 mmol) over 5 minutes. The reaction mixture was warmed to 55 C for 1 hour. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated in vacuo and the resulting solid was washed with ether and filtered to provide 14 g of the desired product (62% yield) in sufficient purity for use in the subsequent reaction: XH NMR (400 MHz, CDC13) delta 7.94 (s, 1H), 5.00 (d, J = 44.2 Hz, 2H), 0.26 (s, 9H) ppm; LCMS Gradient 10-90%, 0.1% formic acid, 5 min, C18/ACN, RT = 3.42 min (M+H) 226.39.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-chloropyrazin-2-amine, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARIFSON, Paul, S.; LEDEBOER, Mark, W.; CLARK, Michael, P.; BOYD, Michael, J.; GAO, Huai; LEDFORD, Brian; MALTAIS, Francois; PEROLA, Emanuele; WO2013/184985; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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 76537-18-3, name: 3-Bromo-5-chloropyrazin-2-amine

A flask was charged with 3-bromo-5-chloropyrazin-2-amine (0.24 g, 1.2 mmol, D-L Chiral Chemicals), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.24 g, 1.2 mmol, Aldrich), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.041 g, 0.058 mmol), and cesium fluoride (0.53 g, 3.5 mmol). tert-Butyl alcohol (6.1 mL) and water (1.6 mL) were added, and the mixture was degassed and heated to 60 C. for 1.5 hours, then at 70 C. overnight, then at 100 C. for 1.5 hours. Upon cooling, the reaction mixture was partitioned between water and EtOAc, and the layers were separated. The aqueous layer was extracted with two additional portions of EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient of 0-10% MeOH in DCM to afford a pale yellow solid (0.14 g, 58%). LCMS for C8H9ClN5 (M+H)+: calculated m/z=210.1; found 210.1.

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-Bromo-5-chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Shepard, Stacey; Combs, Andrew P.; Falahatpisheh, Nikoo; Shao, Lixin; (96 pag.)US2019/276435; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 76537-18-3, These common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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.

First, into a three-neck flask equipped with a reflux pipe were put 5.01 g of 60 3-bromo-5-chloropyrazin-2-amine, 6.04 g of 5 2-methoxynaphthalene-1-boronic acid, 5.32 g of 6 potassium fluoride, and 86 mL of dehydrated tetrahydrofuran, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by being stirred under reduced pressure, and then 0.44 g of 7 tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 3.4 mL of 8 tri-tert-butylphosphine (abbreviation: P(tBu)3) were added thereto. The mixture was stirred at 80 C. for 22 hours to be reacted. After a predetermined time elapsed, the obtained mixture was subjected to suction filtration and the filtrate was concentrated. Then, purification by silica gel column chromatography using a developing solvent (toluene:ethyl acetate=10:1) was performed, so that 5.69 g of a target pyrazine derivative (yellowish white 61 powder) was obtained in a yield of 83%. A synthesis scheme of Step 1 is shown in (e-1) below

Statistics shows that 3-Bromo-5-chloropyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 76537-18-3.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Yamaguchi, Tomoya; Yoshizumi, Hideko; Kido, Hiromitsu; Seo, Satoshi; Sasaki, Toshiki; (180 pag.)US2019/31673; (2019); 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

A solution of the compound 5a (2.20g, 8.00mmol), 3-bromo-5-chloropyrazin-2-amine (1.54g, 7.27mmol), potassium acetate (2.00g, 14.54mmol), Pd (dppf) Cl2 (0.15g, 0.20mmol), H2O (2mL) in dioxane (40mL) was heated to 75 C under N2 for 4 hours. Hexane (50mL) was added, the precipitate was filtered to afford the compound 5b as a brown solid (0.79g, 36%). MS: 277 (M+H) +.

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 76537-18-3.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; CHU, Jie; WU, Xinping; WEN, Chunwei; KANG, Di; BAI, Jinlong; PEI, Xiaoyan; (82 pag.)WO2017/211303; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

A 40 mL vial was charged with 3-bromo-5-chloropyrazin-2-amine (150 mg, 0.72 mmol, Ark Pharm), cesium fluoride (328 mg, 2.16 mmol), 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (178 mg, 0.79 mmol, Combi-blocks), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (13 mg, 0.018 mmol), l-butanol (3 mL), and water (0.75 mL). The mixture was sparged with N2 for 5 min, then heated to 60 C for 1H. The reaction mixture was partitioned between water and EtOAc, and the layers were separated. The organic layer was washed with brine, dried over MgSCL, filtered, and concentrated. The residue was purified by flash chromatography (0-100% EtO Ac/hexanes) to afford the title compound as a tan solid (140 mg, 86%). LCMS calculated for CXFLC1N4S (M+H)+: m/z = 227.0, found: 227.0.

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

Reference:
Patent; INCYTE CORPORATION; SHVARTSBART, Artem; COMBS, Andrew, P.; FALAHATPISHEH, Nikoo; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; (170 pag.)WO2019/126505; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3,Some common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.

Into a three-neck flask equipped with a reflux pipe were put 2.48 g of 3-bromo-5-chloropyrazin-2-amine, 2.19 g of 5-chloro-2-methoxyphenylboronic acid, 2.26 g of potassium fluoride, and 43 mL of tetrahydrofuran, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by being stirred under reduced pressure, and then 0.44 g of tris(dibenzylideneacetone)dipalladium(0) and 4.0 mL of tri-t-butyl phosphine were added thereto. The mixture was reacted by being stirred at 80 C for 42 hours. After a predetermined time elapsed, the obtained mixture was suction-filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography using a developing solvent (toluene: ethyl acetate = 10: 1), whereby 1.00 g of 2,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3- )]pyrazine, which was a target substance, was obtained in a yield of 31 %. A synthesis scheme of Step 1 is shown in (b-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-chloropyrazin-2-amine, its application will become more common.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; YAMAGUCHI, Tomoya; YOSHIZUMI, Hideko; KIDO, Hiromitsu; TAKAHASHI, Tatsuyoshi; SEO, Satoshi; (162 pag.)WO2018/122664; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 76537-18-3, These common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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.

Intermediate C65-Chloro-3-(2-methylthiazol-5-yI)pyrazi n-2-am i ne A mixture of 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thiazole (1 g, 4.44 mmol), 3-bromo-5-chloropyrazin-2-amine (0.926 g, 4.44 mmol), PdCI2(dppf).CH2CI2 adduct (0.181 g, 0.222 mmol) and 2 M Na2CO3 (6.66 ml) in DME (22.21 ml) under N2 was heatedusing microwave radiation at 120C for 45 mins. The mixture was added to water (100 ml) and extracted with EtOAc (2 x 90 ml). The organic extracts were washed with brine, dried over Mg504 and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-10% [2.OM NH3 in MeOH] in TBME afforded the title compound as a brown solid;LCMS: Rt 0.87 mins; MS mlz 227.1 [M+H]+; Method 2minLC_v003.

The synthetic route of 76537-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem