Author: Jessica.F

16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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. Quality Control of Methyl 2-aminopyrazine-3-carboxylate

Step 1: synthesis of methyl 3-bromopyrazine-2-carboxylate (99)To a solution of methyl 3-amino-2-pyrazinecarboxylate (13.06 mmol, 2 g) in hydrobromic acid (13.06 mmol, 7.4 ml, 1.057 g) at 0C was added bromine (38.9 mmol, 2 mL, 6.22 g) drop wise and then a solution of sodium nitrite (33.3 mmol, 2.3 g) in water (4 mL). The reaction was stirred for 2h at 0C and the reaction mixture was extracted with CH2CI2. Organic layer was dried and evaporated to give crude methyl 3- bromopyrazine-2-carboxylate 101 (1.2gr, 43%). (m/z) = 217 and 219 (M+H)+.

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

Reference:
Patent; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-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.

Step 1: Synthesis of 5-bromopyrazin-2-amine To a stirred solution of pyrazin-2-amine (3 g, 31.545 mmol) in anhydrous DCM (30 mL) was added NBS (5.6 g, 31.54 mmol) under nitrogen and stirred at 0 C. for 1 h. Progress of reaction was monitored by TLC. After reaction completion DCM was added and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 70% DCM/hexane to 10% ethyl acetate in hexane as eluent to yield 5-bromopyrazin-2-amine (3.4 g, 62.9%) as white solid. MS: 175.1 [M++1]

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); 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. 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 1245644-42-1

General procedure: [0194] 6-bromo-3-iodo-imidazo[1,2-a]pyrazine 17* (0.648 g, 2 mmol) was added to a degassed mixture of dioxane(10 ml) and water (1.5 ml). The aromatic boronic acid (R2B(OH)2) (2.2 mmol) was added followed by palladium acetate(0.022 g, 5 mol%), triphenyl phosphine (0.025 g, 5 mol%) and sodium carbonate (0.32 g, 3 mmol). The reaction mixturewas stirred at 80 C under nitrogen for 18 hours. The solvent was evaporated in vacuo and the residue was partitionedbetween water (20 ml) and dichloromethane (50 ml). The dichloromethane was separated, dried over magnesium sulphateand evaporated in vacuo. The residue was purified by flash chromatography.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (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. 126069-70-3, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 126069-70-3

2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (1.06 g, 5.55 mmol, Intermediate 4) and triethylamine (0.850 ml, 6.10 mmol) were dissolved in dichloromethane (DCM) (25 ml). 2-chloro-3-(trifluoromethyl)benzoyl chloride (1.348 g, 5.55 mmol) was added and the mixture stirred at room temperature for 24 h. The solvents were removed in vacuo and the solid partitioned between dichloromethane (100 ml) and saturated sodium bicarbonate solution (50 ml). The aqueous phase was extracted with dichloromethane (3 x 50ml), the combine organic extracts were dried over anhydrous sodium sulfate and then concentrated to afford 7-{[2-chloro-3- (trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1 ,2- a]pyrazine (2.22 g, 5.58 mmol, 101 % yield). LC/MS [M+H]+ = 398, 400, retention time = 1.04 minutes (2 minute method).

The synthetic route of 126069-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 21943-17-9, A common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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.

General procedure: A solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

The synthetic route of 21943-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H4BrN3

Into a 20-L 4-necked round-bottom flask was placed a solution of 5-bromopyrazin-2-amine (400 g, 2.30 mol) in ethylene glycol dimethyl ether (8 L) , iodocopper (131 g, 687.84 mmol) , diiodane (293 g, 1.15 mol) , iodopotassium (380 g, 2.29 mol) and 3-methylbutyl nitrite (1800 mL, 11.5 mol) . The resulting solution was stirred for 30 min at 60 C, then extracted with 2 x 10 L of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford the title compound.

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; MERCK SHARP & DOHME CORP.; DEBENHAM, John S.; COX, Jason M.; LAN, Ping; SUN, Zhongxiang; FENG, Zhe; SUN, Chunrui; SEGANISH, W. Michael; LAI, Zhong; ZHU, Chen; BARA, Thomas; RAJAGOPANALAN, Murali; DANG, Qun; KIM, Hyunjin M.; HU, Bin; HAO, Jinglai; (112 pag.)WO2018/107415; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, 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 41270-66-0, Recommanded Product: 5-Chloro-2,3-diphenylpyrazine

5 gm of 2-chloro-5,6-diphenylpyrazine (IV) in 25 ml N-Methyl-2-pyrrolidone (NMP) and 5.18 gm of K2CO3 were mixed with 9.92 gm of 4-(isopropylamino)-l-butanol (III), the reaction mixture was then heated with stirring at 150-155 C for 20-21 hrs. The reaction solution was air-cooled, poured into 25 ml water, extracted with 20 ml ethyl acetate. Aqueous layer washed with 10 ml ethyl acetate. Ethyl acetate layers are combined and washed with 15 ml of water, dried over anhydrous magnesium sulfate and then concentrated to obtain 6.3 gm of residue. 6 gm of the residue was purified by silica gel column chromatography by eluting with 2000 ml hexane and 550 ml ethyl acetate to obtain solid 3.2 gm of the desired compound. Yield: 49.41 %

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; LUPIN LIMITED; RAY, Purna, Chandra; KUMAR, Gaurav; SHABADE, Samir, Shanteshwar; RASHINKAR, Dattatray, Bajirao; ARORA, Surinder, Kumar; SINGH, Girij, Pal; (23 pag.)WO2017/60827; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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.

Step 1 To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIV) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95 C. for 3 hours. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1:1) to yield tert-butyl (1-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXVI) (2.2882 g, 8.04 mmol, 83.9% yield) as a white solid. ESIMS found for C12H17ClN4O2 m/z 285.1 (M+H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); 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 1196152-38-1 as follows. Application In Synthesis of 2-Bromo-5-(trifluoromethyl)pyrazine

example 3o (100 mg, 0.55 mmol), 2-Chloropyrimidine (76.3 mg, 0.67 mmol) and N,N- diisopropylethylamine (192 mu, 1.11 mmol) are dissolved in 1 ml of DMSO and the reaction mixture is heated in a microwave reactor 30 minutes at 120C. The crude product is partitioned between Et20 and water; the organic layer is then separated and concentrated under reduced pressure to obtain the title compound (158 mg). UPLC-MS (Method 2): Rt = 0.76 MS (ES+): m/z = 259 [M+H]+ . Example 30a is synthesized as described for example 28a using example 3o (600 mg, 3.3 mmol), 2-Bromo-5-(Trifluoromethyl)pyrazine (907 mg, 4.0 mmol) instead of 2- Chloropyrimidine, N,N-diisopropylethylamine (1.1 ml, 6.7 mmol) and 8 ml of DMSO. The mixture is heated in a microwave reactor at 100C during 2.5 hours. The crude product is partitioned between EtOAc and water then the organic layer is separated and concentrated under reduced pressure; the residue is purified by Silica gel flash chromatography, using EtOAc/Cyclohexane 1 : 1 to EtOAc 100% as eluent, to obtain the title compound (800 mg, 72 % yield). HPLC-MS (Method 5): Rt = 3.21 MS (APCI+): m/z = 327 [M+H]+ .

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 29 5- [2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-PROPIONYLAMINO]- PYRAZINE-2-CARBOXYLIC acid HYDROXYAMIDE [000197] A solution of methyl 5-chloropyrazine-2-carboxylate (30.00 g, 0.17 mol) in tetrahydrofuran (87 mL) was treated with a solution of potassium carbonate (72.08 g, 0.52 mol) in water (261 mL). The resulting reaction mixture stirred at 25C for 42 h. The reaction mixture was then acidified to a pH of about 2 with concentrated hydrochloric acid, diluted with a saturated aqueous sodium chloride solution (300 mL), and was continuously extracted with ethyl acetate (4L total) until no product was present in the aqueous layer. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-chloro-pyrazine-2-carboxylic acid (26.54 g, 96%) as an off-white solid: mp 150-151C ; EI-HRMS m/e calcd for CSH3CIN202 (M 157.9883, found 157.9877.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem