Month: May 2021

Electric Literature of 33332-30-8, 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 33332-30-8 as follows.

Example 90 2-Methoxy-6-(‘4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl’)pyrazine-; A mixture of 2-chloro-6-methoxypyrazine (0.50 g, 3.46 mmol), bis(pinacolato)diboron (0.966 g, 3.80 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.095 g, 0.10 mmol), tricyclohexyl phosphine (0.116 g, 0.42 mmol) and potassium acetate (0.509 g, 5.19 mmol) in 1,2-dimethoxy ethane (10 mL) was run for 3h at 15O0C in a microwave oven under argon atmosphere. The reaction mixture was partitioned between water and diethyl ether and the organic phases were pooled, dried over magnesium sulfate, filtered and concentrated to give 1.15 g (quantative yield) of the crude title compound which was used in the next reaction step without further purification; MS (CI) m/z 237.

According to the analysis of related databases, 33332-30-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145571; (2007); 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. 100047-56-1, name is 5-Bromo-3-methylpyrazin-2-ol, A new synthetic method of this compound is introduced below., Formula: C5H5BrN2O

(ls,4s)-4-(l-Methylpiperidin-4-yloxy)cyclohexanol (1.2 g, 5.63 mmol) was dissolved inTHF (10 mL), 5-bromo-3-methylpyrazin-2-ol (1.170 g, 6.19 mmol) and triphenylphosphine (1.771 g, 6.75 mmol) were added, then cooled down in an ice -water bath. DIAD (1.329 ml, 6.75 mmol) was added dropwise under N2. The reaction mixture was slowly warmed to room temperature, stirred overnight, and concentrated. The residue was purified by preparative HPLC (15-80% CH3CN/H20 with 0.1 % TFA over 30 min) and column chromatography (5% methanol/ethyl acetate containing 1 % Et3N) to give the title compound (525 mg, 1.366 mmol, 24.3% yield). Exact mass calculated for Ci7H26BrN302: 383.1 , found: LCMS m/z = 384.2[M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.45-1.62 (m, 4H), 1.65-1.75 (m, 2H), 1.91-2.05 (m, 4H), 2.05-2.15 (m, 2H), 2.39 (s, 3H), 2.36-2.42 (m, 2H), 2.42 (d, J = 0.7 Hz, 3H), 2.78-2.85 (m, 2H), 3.46-3.54 (m, 2H), 4.95-5.02 (m, 1H), 7.98 (d, J = 0.6 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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine, 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 6-Bromo-5-methylpyrazin-2-amine

A mixture of compound 15a (100 g, 0.53 mol) and ClCH2CHO (500 g (400 mL), 3.20 mol, 50 wt % aqueous solution) in H2O (600 mL) was refluxed for 5 h. The reaction mixture was concentrated to remove ClCH2CHO then extracted with EtOAc (600 mL¡Á3). The combined organic layers were concentrated and recrystallized from EtOAc and petroleum ether. The mother liquor was purified by column chromatography eluted with petroleum ether/EtOAc (2:1?1:1) to give 5-bromo-6-methylimidazo[1,2-a]pyrazine 1 (50 g, 44%) as a yellow solid; mp 145-148 C; IR (KBr): 3100, 1495, 1324, 1295, 1145, 771 cm-1; 1H NMR (400 MHz, CDCl3): delta=8.99 (s, 1H), 7.87-7.84 (m, 2H), 7.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=140.0 (2C), 139.0, 134.8, 115.0, 110.4, 22; HRMS-ESI: calcd for C7H7BrN3 (M+H)+: 211.9823 and 213.9803; found: 211.9817 and 213.9797.

The synthetic route of 74290-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Harris, Anthony R.; Nason, Deane M.; Collantes, Elizabeth M.; Xu, Wenjian; Chi, Yushi; Wang, Zhihan; Zhang, Bingzhi; Zhang, Qingjian; Gray, David L.; Davoren, Jennifer E.; Tetrahedron; vol. 67; 47; (2011); p. 9063 – 9066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1166831-45-3,Some common heterocyclic compound, 1166831-45-3, name is Methyl 6-chloro-3-methylpyrazine-2-carboxylate, molecular formula is C7H7ClN2O2, 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 solution of methyl 6-chloro-3-methylpyrazine-2-carboxylate (8.6 g, 46.1 mmol) and hydrogen peroxide urea adduct (8.1 g, 86 mmol) in dichloromethane (100 mL) was added 2,2,2-trifluoroacetic anhydride (10.9 ml, 78 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with DCM and quenched with water. The aqueous layer was extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the crude product 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol, 95% yield) which was used without further purification. 1H NMR (300 MHz, CDCl3) delta ppm 8.31 (1H, s), 4.02 (3H, s), 2.65 (3H, s).

The synthetic route of 1166831-45-3 has been constantly updated, and we look forward to future research findings.

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

Related Products of 38557-71-0, 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 38557-71-0 as follows.

To a suspension of 2-chloro-6-methylpyrazine (24 g, 186.7 mmol) in anhydrous MeOH (240 mL) was added NaOMe (12.1 g, 224 mmol). The mixture was stirred at 60-70C for 16 hours. The mixture was cooled and filtered. The filtrate was concentrated in vacuo to give 2- methoxy-6-methylpyrazine (22 g, 95% yield). 1H NMR (CDCI3400 MHz): delta 7.98 (s, 1 H), 7.94 (s, 1 H), 3.91 (s, 3H), 3.40 (s, 3H). LC-MS: t = 1.47 min (method 14), m/z = 124.8 [M + H]+.

According to the analysis of related databases, 38557-71-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 723286-67-7, name is Ethyl 1,2,4-Triazolo[4,3-a]pyrazine-3-carboxylate, 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: 723286-67-7

A mixture of 380 mg of ethyl [1, 2,4] triazolo [4,3-a] pyrazine-3-carboxylate from Step B and 50 mg of 10% palladium on carbon in 10 ML of ethyl acetate and 10 mL of ethanol was stirred under an atmosphere of hydrogen for 18 h. The mixture was filtered through a pad of Celite and the filtrate concentrated to give the title compound as a solid. LC/MS 169 (M+1).

The synthetic route of Ethyl 1,2,4-Triazolo[4,3-a]pyrazine-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5910-89-4,Some common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, molecular formula is C6H8N2, 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.

A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g, 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 700C for 220 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at25 ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).

The synthetic route of 5910-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/100461; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 476622-89-6, name is 5-Bromo-2-iodo-3-methoxypyrazine, 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. SDS of cas: 476622-89-6

General procedure: In a Schlenk flask, a solution containing the haloheterocycle (1mmol), the boronic acid (1.3mmol), methanol (5mL) and a 2M aqueous sodium carbonate solution (3.35mmol) in benzene (25mL) was deoxygenated by bubbling a stream of argon through it. Pd(PPh3)4 (0.14mmol) was then added and the flask was evacuated and purged with argon. The reaction mixture was heated for the time indicated and the reaction was quenched with water and extracted with CH2Cl2 (3¡Á). The combined organic extracts were dried over Na2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel as indicated.

The synthetic route of 5-Bromo-2-iodo-3-methoxypyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Garcia-Rodriguez, Jose; Perez-Rodriguez, Santiago; Ortiz, Maria A.; Pereira, Raquel; De Lera, Angel R.; Piedrafita, F. Javier; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1285 – 1302;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13457-28-8, name is Methyl 3-bromo-6-chloropyrazine-2-carboxylate, 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 13457-28-8, Quality Control of Methyl 3-bromo-6-chloropyrazine-2-carboxylate

To a 250 ml three-neck flask was added 50 ml of tetrahydrofuran, 50 ml of water, and Compound 3 (20 g, 0.08 mol). Lithium hydroxide monohydrate (5 g, 0.12 mol) in water/70 ml of water was added dropwise. The reaction was completed at 0C for 1 hour. The reaction is complete. Methyl tert-butyl ether extraction (30 ml x 2). The aqueous phase was adjusted to pH=1 with 4N hydrochloric acid and extracted with dichloromethane (50 ml¡Á3). Dry 10 g of anhydrous sodium sulfate and spin-dry to obtain white solid compound 4 (18 g, yield 96%).

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; Shaoyuan Science And Technology (Shanghai) Co., Ltd.; Shanghai Shaoyuan Reagent Co., Ltd.; Wei Yuanbo; Guo Tao; Wu Yong; (8 pag.)CN108101857; (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. 213019-67-1, name is 3-(Trifluoromethyl)pyrazin-2-amine, A new synthetic method of this compound is introduced below., Product Details of 213019-67-1

[1388] A solution of 3-(trifluoromethyl)pyrazin-2-amine (0.075 g, 0.460 mmol) [Oakwood, 500509] in dichloromethane (1.88 mL) was treated with N-bromosuccinimide (0.082 g, 0.460 mmol) and stirred at rt for 15 h. The reaction mixture was treated with additional N-bromosuccinimide (0.041 g, 0.230 mmol) and stirred for 21 h. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (220 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to brown, oily-solid. Purification by flash column chromatography using EtOAc in hexanes (0% to 30%) gave the desired product (64.5 mg, 58.1%) as a white solid. LCMS for C5H4BrF3N3(M+H)+: m/z=242.0, 243.9; Found: 241.9, 243.9.

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; Incyte Corporation; Douty, Brent; Ai, Yanran; Burns, David M.; Combs, Andrew P.; Falahatpisheh, Nikoo; Levy, Daniel; Polam, Padmaja; Shao, Lixin; Shepard, Stacey; Shvartsbart, Artem; Yue, Eddy W.; (132 pag.)US2020/2295; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem