Month: February 2021

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, Recommanded Product: 2-Bromopyrazine

General procedure: A mixture of methyl 4-bromobenzoate2a (100 mg, 0.465 mmol), methyl N-(tert-butoxycarbonyl)glycinate 3a (132 mg, 0.698 mmol), Pd2(dba)3 (8.5 mg,9.3 lmol), Xantphos (16 mg, 0.028 mmol), and cesium carbonate(303 mg, 0.930 mmol) was charged with dioxane (1.0 mL). Theresulting suspension was sparged with argon via subsurface bubblingfor 5 min, and the reaction mixture was sealed and stirredat 100 C for 12 h. The reaction was cooled to ambient temperature,diluted with EtOAc (20 mL), and filtered to remove the inorganicsalts. The filtrate was concentrated to an oil, then purified bycolumn chromatography on silica gel, eluting with an EtOAc/hexanesgradient (2-30%) to afford the desired product 4a as a colorlessgum (75% isolated yield). 1H NMR (500 MHz, DMSO-d6): d 7.90(d, J = 9.0 Hz, 2H), 7.40 (d, J = 8.5 Hz, 2H), 4.39 (s, 2H), 3.83 (s, 3H),3.68 (s, 3H), 1.37 (s, 9H). LRMS (ESI) calcd for C16H21NO6 (M+Na)+:346.1, found: 346.1.

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:
Article; Falcone, Danielle; Osimboni, Ekundayo; Guerin, David J.; Tetrahedron Letters; vol. 55; 16; (2014); p. 2646 – 2648;,
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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7N3O2

Example 3a Methyl 3-amino-6-iodopyrazine-2-carboxylate 1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide The reaction medium is heated at 65 C. for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65 C. for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+1) 280 1H NMR: deltaH ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

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 16298-03-6.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; US2013/85144; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 16298-03-6, These common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-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.

Hydrazine monohydrate (34 mL, 1094.95 mmol) was added portionwise to a stirred suspension of methyl 3-aminopyrazine-2-carboxylate (21.3 g, 139.09 mmol) in ethanol (65 mL) at r.t. The resulting slurry was stirred at 60¡ã C. for 2 hours, cooled to room temperature and filtered. The solid was washed with cold ethanol (2*25 ml) and dried to a constant weight to afford 3-aminopyrazine-2-carbohydrazide (20.75 g, 97percent) as a beige solid: 1H NMR Spectrum; (DMSO-d6) 4.49 (2H, d), 7.46 (2H, br s,), 7.78 (1H, d), 8.17 (1H, d), 9.79 (1H, t); Mass Spectrum [M+H]+=154.

Statistics shows that Methyl 2-aminopyrazine-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 16298-03-6.

Reference:
Patent; ASTRAZENECA AB; BARLAAM, Bernard Christophe; DELOUVRIE, Benedicte; OUVRY, Gilles; LAMBERT-VAN DER BREMPT, Christine Marie, Paul,; HARRIS, Craig Steven; BERRY, David; TOMKINSON, Gary Peter; REID, Gary Patrick; US2014/206700; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 95-89-6,Some common heterocyclic compound, 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, molecular formula is C6H7ClN2, 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.

Preparation 17: 2 5-dimethVL-3-94-(phenylmethyl) piperazin-1-VLLpyrazine 3-Chloro-2, 5-dimethylpyrazine (1.0 g, 7.0 MMOL) and N-benzylpiperazine (3.7 ML, 21.0 MMOL) were mixed under nitrogen and heated to 125 C for 18 h. Saturated aqueous sodium hydrogen carbonate was added and the product was extracted with chloroform. The combined organic extracts were dried (NA2SO4) and concentrated in vacuo to give a yellow oil. The crude product was purified by flash chromatography using silica gel eluting with methanol : chloroform (2.5 : 97.5) to give the pure product as a yellow oil (1.14 g, 58%).

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/72086; (2004); A2;,
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 59489-71-3 as follows. Computed Properties of C4H4BrN3

EXAMPLE 1B 5-amino-2-pyrazinecarbonitrile A mixture of Example 1A (19.29 g, 105 mmol), freshly powdered KCN (16.9 g, 260 mmol), CuI (49.5 g, 260 mmol), 18-crown-6 (2.08 g, 7.8 mmol), and (PPh3)4Pd (1.8 g, 1.57 mmol) in N,N-dimethylformamide (600 mL) was stirred at room temperature for 30 minutes and heated to reflux in an oil bath preheated to about 200 C. The solution was stirred at reflux for 3 hours, cooled to room temperature, poured into ethyl acetate (1 L), filtered through diatomaceous earth (Celite), treated with silica gel (100 g), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 11.9 g (94.4%) of the desired product. MS (APCI(+)) m/z 121 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.40 (d, J=0.7 Hz, 1H), 7.90 (d, J=0.7 Hz, 1H), 7.47-7.69 (br s, 2H).

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 122-05-4, 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 122-05-4 as follows.

A mixture of pyrazine-2, 5-dicarboxylic acid (4.0Og, 23.79mmol) and hydrochloric acid (1 M in ethanol) was sealed in a pressure vessel and heated to 800C for 48 hours. The cloudy mixture was filtered through a short pad of celite and the filtrate was concentrated under vacuum. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated under vacuum to obtain the title compound (1.84g). MS (ESI) m/z 225.0 [M+H]+

According to the analysis of related databases, 122-05-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2009/24550; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 6 6-Chloro-N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 3.04 (10 mmols) of methyl 6-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 1.5 g (12 mmols) of 2-amino-6-chloro-pyrazine were reacted in 150 ml of xylene analogous to Example 2. 3.2 g (80percent of theory) of 6-chloro-N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained. Melting point: 283¡ã-284¡ã C. (from dioxane). C14 H10 Cl2 N4 O4 S (401.23): Calc.: C–41.91percent; H–2.51percent; N–13.96percent; Cl–17.67percent; S–7.99percent. Found: C–42.05percent; H–2.62percent; N–14.09percent; Cl–17.54percent; S–7.80percent.

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-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1320266-90-7, name is 8-Chloro-3-isopropylimidazo[1,5-a]pyrazine, 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 1320266-90-7, category: Pyrazines

Intermediate J (33 mg, 0.17 mmol) dissolved in 0.18 mL of DMF was added to NIS (39 mg, 0.17 mmol) dissolved in 0.6 mL of DMF. The reaction mixture was heated to 60 C for 3 h and then cooled to room temperature. The reaction mixture was partitioned between 1 M a2S03 and dichloromethane. The aqueous layer was then extracted with dichloromethane (3X). The organic layers were combined, dried over a2S04 and concentrated in vacuo to afford 34 mg (62% yield) of pure Intermediate K. .H-NMR (300 MHz, CDC13) delta 1.41 (d, 6H, / = 6.9 Hz), 3.20-3.31 (m, 1H), 7.28 (d, 1H, J= 5.1 Hz), 7.65 (d, 1H, J = 5.1 Hz). MS (ESI) (M+H)+ 322.1.

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; UNIVERSITY OF WASHINGTON; VAN VOORHIS, Wesley, C.; HOL, Wilhelmus, G.J.; LARSON, Eric, T.; MALY, Dustin, James; MERRITT, Ethan; OJO, Kayode, K.; WO2011/94628; (2011); 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. 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, A new synthetic method of this compound is introduced below., Product Details of 1053656-22-6

To a solution of the boc-ester (1 g, 3.38 mmol) obtained from step-3 in dry toluene (40 ml) was added DIBAL (1M, 3.7 mmol) at -78 C. and the reaction mixture was allowed to stir at this temperature for 5 hrs (monitored by TLC). Reaction was quenched with methanol (3.7 ml) and was slowly brought to 25 C. Brine (10 ml) was added to it and filtered through celite bed. Residue was washed with dichloromethane and combined organic layer was evaporated to get the crude aldehyde, which was used directly in the next step without any further purification. Yield: 800 mg (crude)

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; GRUENENTHAL GmbH; US2009/186899; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 109838-85-9, 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(2S,5R)-2-((2,3-Dihydrobenzo[b][l,4]dioxin-6-yl)methyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine. n-BuLi (57 mL, 142 mmol, Aldrich) was added dropwise to a solution of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (24 g, 132 mmol) in THF (200 mL) at -78 0C under N2, and the mixture was stirred at the same temperature for 40 minutes. A solution of 6-(bromomethyl)-2,3- dihydrobenzo[b][l,4]dioxine (27 g, 118 mmol) in THF (160 mL) was added dropwise, and the resulting mixture was stirred at -78 0C for an additional 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl (200 mL). The THF was then removed under reduced pressure, and the resulting mixture was partitioned between EtOAc (300 mL) and H2O (300 mL). The organic layer was separated, washed with brine (300 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (100: 1 to 30: 1) to afford (2S,5R)-2-((2,3-dihydrobenzo[b][l,4]dioxin-6-yl)methyl)-5-isopropyl-3,6- dimethoxy-2,5-dihydropyrazine (34 g, 73 percent). LCMS (API-ES) m/z 333.2 (M+H+).

The synthetic route of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; ZENG, Qingping; YUAN, Chester Chenguang; YAO, Guomin; WANG, Xianghong; TADESSE, Seifu; ST. JEAN, JR., David J.; REICHELT, Andreas; LIU, Qingyian; HONG, Fang-Tsao; HAN, Nianhe; FOTSCH, Christopher H.; DAVIS, Carl D.; BOURBEAU, Matthew P.; ASHTON, Kate S.; ALLEN, John G.; WO2010/83246; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem