Month: March 2021

Electric Literature of 710322-57-9,Some common heterocyclic compound, 710322-57-9, name is Methyl 5-formylpyrazine-2-carboxylate, molecular formula is C7H6N2O3, 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.

Methyl 5-(hvdroxymethyl)pyrazine-2-carboxylate 29-(l)To a solution of methyl 5-formylpyrazine-2-carboxylate (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (I N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3 x 40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, IH), 9.27 (s, IH)

The synthetic route of 710322-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; ELLARD, John Mark; FARTHING, Christopher Neil; HALL, Adrian; WO2011/9898; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Synthesis o -chloro-6-phenylpyrazine[00145] To a solution of 2,6-dichloropyrazine (2.0 equiv.) in 3 : 1 DME:2M aqueous sodium carbonate (0.125 M) was added phenylboronic acid (1.0 equiv.) then PdCl2(dppf) ¡¤ DCM adduct (0.1 equiv.). The reaction was heated in the microwave at 120 C for 15 minutes. The crude reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium bicarbonate then sat. NaCl. The organic phase was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel column chromatography with heptanes to 30% ethyl acetate in heptanes to give 2- chloro-6-phenylpyrazine in 75% yield. LC/MS (m/z): 191.0 (MH+), R, = 1.00 min.

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; NOVARTIS AG; BURGER, Matthew; DING, Yu; HAN, Wooseok; LINDVALL, Mika; NISHIGUCHI, Gisele A.; RICO, Alice; SMITH, Aaron; TANNER, Huw; WAN, Lifeng; WO2012/4217; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59489-71-3, name is 2-Amino-5-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 59489-71-3, Recommanded Product: 2-Amino-5-bromopyrazine

2-Amino-5-bromo-pyrazine (20) (1,170mg, 6.72mmol), was dissolved in iodomethane (CH3I) (1.2ml, 19.5mmol) in tetrahydrofuran (THF) (100ml). The solution was cooled to 0 C., 60% sodium hydride (NaH) (1.5g, 37.5mmol) was added slowly and the mixture was stirred for 5 hours. A small amount of methanol was added to the reaction mixture, an excess of iodomethane, to decompose sodium hydride. Followed by water (10ml) was added and extracted with ethyl acetate (3 ¡Á 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography [silica gel 48.5 g; hexane – ethyl acetate (1: 1)] and purified by, 2-dimethylamino-5-bromo-pyrazine (21) (1,096mg, 5.4mmol , 80%) as a pale yellow powdered 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-Amino-5-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF ELECTRO-COMMUNICATIONS; MAKI, SHOJIRO; NIWA, HARUKI; (25 pag.)JP2015/193584; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 138588-41-7, 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 138588-41-7 as follows.

EXAMPLE 263 1-Isopropyl-3-methyl-5-(2-pyrazin-2-yl-5-m-tolyl-1H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one A stirred mixture of 5-(bromo-m-tolyl-acetyl)-1-isopropyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (prepared as described in example 142, 0.5 gm, 1.25 mmol), pyrazine-2-carboxamidine hydrochloride (0.395 gm, 2,49 mmol) cesium carbonate (1.22 gm, 3.74 mmol) and DMF (4.0 mL) was heated to 60 C. After 1 hour, the reaction was determined to be complete by LCMS. The reaction was cooled to room temperature and diluted with water (40 mL). After stirring for 1 hour, the crude suspension was filtered and the solids were purified by flash chromatography (diethyl ether, followed by ethyl acetate) to afford 40 mg of the title compound as a light tan solid. MS (M+1)=425.1

According to the analysis of related databases, 138588-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US2003/92749; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-Chloropyrazine, 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 14508-49-7, COA of Formula: C4H3ClN2

[Referential Example 2] 2-Hydrazinopyrazine [Show Image] Hydrazine monohydrate (21.80 g) was added to 2-chloropyrazine (10.44 g) in ethanol (65 mL) at room temperature, and the resultant mixture was refluxed for 17 hours, followed by cooling in air. The reaction solvent was evaporated under reduced pressure, and then benzene was added to the residue. The resultant mixture was subjected to decantation, to thereby remove an insoluble matter. The benzene was evaporated under reduced pressure. Hexane was added to the resultant solid, and the mixture was subjected to filtration, to thereby give the title compound (4.67 g, 47%). 1H-NMR(400MHz,CDCl3)delta:7.89(1H,d,J=2.7Hz), 7.99-8.05(1H,m), 8.20(1H,d,J=1.5Hz). ESI-MS m/z:111(M+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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1762568; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-58-4, These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-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.

l-Chloro-N,N-2-trimethylpropenylamine (0.08 mL, 0.60 mmol) was added to a solution of 3 – { [5-(azetidin- 1 -ylcarbonyl)-3 -chloropyridin-2-yl] oxy } -5 – { [2-fluoro- 1 – (fluoromethyl)ethyl]oxy}benzoic acid (215 mg, 0.5 mmol) in DCM (5 mL) and the reaction stirred at RT for 30 – 40 minutes. Pyridine (0.08 mL, 1.0 mmol) and 2-amino-5- methylpyrazine (108 mg, 1.0 mmol) were added and the reaction stirred for 16 hours before being concentrated in vacuo and water (20 mL) added. The mixture was extracted with ethyl acetate (3 x 20 mL), washed with IN hydrochloric acid (20 mL), a saturated solution of sodium hydrogen carbonate (20 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0-10% methanol in DCM, to give the desired compound as a white solid (150 mg). 1H NuMR delta (CDCl3): 2.40 (quintet, 2H), 2.56 (s, 3H), 4.22-4.31 (m, 2H), 4.32-4.40 (m, 2H), 4.62 – 4.82 (m, 5H), 7.06 (t, IH), 7.38 (t, IH), 7.47 (t, IH), 8.15 (s, IH), 8.17 (s, IH), 8.25 (d, IH), 8.46 (s, IH), 9.55 (s, IH); m/z 518 (M+H)+, 516 (M-H)”

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 123-32-0, 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. 123-32-0, name is 2,5-Dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Example 7 BSc4354: 2,5-Bis(4-methoxystyryl)pyrazine Synthesis: 2,5-Dimethylpyrazine (0.125 g, 1.16 mmol) is dissolved in 10 ml dimethylformamide, followed by addition of 4-methoxybenzaldehyde (0.315 g, 2.32 mmol) and potassium-t-butoxide (0.26 g, 2.32 mmol) The solution is heated for 4 h to 80 C. and allowed to cool to room temperature. In this process, a solid crystallizes out. The solution containing the crystallized solid is filtered and washed with ethyl acetate. After drying under high-vacuum, 0.370 g (yield: 93%) of the product BSc4354 is obtained as yellow solid.1H-NMR (CDCl3, 500 MHz): delta=8.54 (s, 2H), 7.67 (d, J=16 Hz, 2H), 7.55 (d, J=9 Hz, 4H), 7.04 (d, J=16 Hz, 2H), 6.93 (d, J=9 Hz, 4H, 3.85 (s, 6H) ppm13C-NMR (CDCl3, 125 MHz): delta=158.3, 146.9, 141.0, 131.7, 126.7, 120.0, 112.3, 53.4 ppm.

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

Reference:
Patent; KLINIKUM DARMSTADT GMBH; TECHNISCHE UNIVERSITAT DARMSTADT; LUDWIG-MAXIMILIANS-UNIVERSITAT MUNCHEN; Schmidt, Boris; Kieser, Daniel; Bolaender, Alexander; Herms, Jochen; Haussen, Roland Heyny-Von; Gu, Jiamin; US2013/287700; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59489-32-6, name is 5-Chloro-2,3-dimethylpyrazine, 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 59489-32-6, category: Pyrazines

A. 2-(2-Dimethylaminoethylamino)-5,6-dimethyl pyrazine. 2-chloro-5,6-dimethylpyrazine (12.8 g., 0.09 mole) is added to unsym-dimethylethylenediamine (26 g., 0.295 mole) containing cuprous chloride (0.25 g.) and the mixture is heated for 48 hours in an oil bath maintained at 135-140 C. On cooling, 50 ml of water and a single molar excess of 10N sodium hydroxide are added. The mixture is extracted with methylene chloride. The organic extracts are backwashed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under vacuum. The residual oil is dissolved in hexane, filtered and reconcentrated to obtain the product oil (15.8 g., 0.081 mole).

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; Merck & Co., Inc.; US4144338; (1979); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 72788-94-4, 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. 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

D. Synthesis of (6S)-2-nitro-6-({5-[4-(trifluoromethoxy)phenyl]-2-pyrazinyl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (4) by the method of Scheme 3 Et3N (4.17 mL, 29.9 mmol) and mesyl chloride (1.57 mL, 20.3 mmol) were added to a solution of (5-chloro-2-pyrazinyl)methanol (45) (obtained by chlorination and reduction of 5-hydroxypyrazine-2-carboxylic acid, as reported by Kiener et al., 1994) (1.443 g, 9.98 mmol) in anhydrous THF (20 mL) at 0 C. The mixture was stirred at 0 C. for 0.5 h, then partitioned between EtOAc and water. The organic fraction was dried (MgSO4) and the solvent was removed under reduced pressure to give the crude mesylate. The mesylate was dissolved in acetone (40 mL), sodium iodide (7.5 g, 50 mmol) was added, and the mixture was refluxed for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic fraction was concentrated under reduced pressure and the residue was chromatographed on silica gel (eluting with CH2Cl2) to give 2-chloro-5-(iodomethyl)pyrazine (46) (1.54 g, 61%), which was used immediately due to its instability.

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-Chloro-5-(hydroxymethyl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Global Alliance for TB Drug Development; US2012/28973; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 944709-42-6, 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. 944709-42-6, name is 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

6,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (22.1 g, 80 mmol) and 1H-pyrazol-4-aminehydrochloride (10.0 g, 84 mmol) were combined in DMF (398 mL). Triethylamine (33.3 mL, 239mmol) was added and the mixture was heated to 95 ¡ãC for 18 h. The reaction mixture was thencooled to ambient temperature and concentrated under reduced pressure. The residue was suspendedin water (300 mL) and sonicated and filtered. Trituration in ether provided 6-bromo-N-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (19.3 g, 68.9 mmol, 87percent); 1H NMR (400MHz, DMSO-d6) delta 12.67 (s, 1H), 10.65 (s, 1H), 8.54 (s, 1H), 8.10 (s, 1H), 7.82 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; George, Dawn M.; Huntley, Raymond J.; Cusack, Kevin; Duignan, David B.; Hoemann, Michael; Loud, Jacqueline; Mario, Regina; Melim, Terry; Mullen, Kelly; Somal, Gagandeep; Wang, Lu; Edmunds, Jeremy J.; PLoS ONE; vol. 13; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem