Tag: M.W=100-200

Reference of 41110-33-2, 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. 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To the starting material methyl 5-methylpyrazine-2-carboxylate (500 mg 3.3 mmol), THF was added and this was cooled to -78 C, followed by the addition of a 1.0 M methylenechloride solution of DIBAL-H (590 mg 3.6 mmol) and the mixture was stirred for 6 h at-78 C. TLC revealed very little starting material (>5%). The reaction mixture wasremoved from the dry ice bath and was quenched as per Fieser workup. Then 0.14 mLof water was slowly added followed by the addition of ethyl acetate 15 mL, add 0.14 mL15% aqueous sodium hydroxide. Then 0.36 mL water was added, warmed to rt and stirredfor 15 min after addition of Na2SO4 (250 mg). The reaction mixture was filtered over Hyflobed and the bed was washed thoroughly with EtOAc (50 mL). The organic layer wasevaporated under reduced pressure to dryness and purified using silica-gel flashchromatography. The pure product was characterized by NMR. Yield: 78%

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, Methyl 5-methylpyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Balasubramaniam, Sivaraman; Vijayan, Sajith; Goldman, Liam V.; May, Xavier A.; Dodson, Kyra; Adhikari, Sweta; Rivas, Fatima; Watkins, Davita L.; Stoddard, Shana V.; Beilstein Journal of Organic Chemistry; vol. 16; (2020); p. 628 – 637;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 41110-34-3, 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. 41110-34-3, name is Ethyl 5-methylpyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5-methyl-2-pyrazinecarboxylic acid ethyl ester (2) (0.01 mol) and hydrazine hydrate (0.02mol) in ethyl alcohol (20 mL) was refluxed for 3 h with consistent stirring. After realization of the reaction (examined by the TLC), the reaction mixture is cooled to room temperature and filtered. The crude product was recrystallized from ethanol to offer pure 5-methyl-2-pyrazine carboxylic acid hydrazide (3).

The synthetic route of Ethyl 5-methylpyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maddireddi, Chandra Sekhara Reddi; Parimi, Uma Devi; Reddy, Sreenivasa Reddy Bhimi; Mandapati, Satyanarayana Reddy; Asian Journal of Chemistry; vol. 28; 11; (2016); p. 2453 – 2456;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 74290-69-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74290-69-0 name is 5-Bromo-6-methylpyrazin-2-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 6: methyl 5-amino-3-methylpyrazine-2-carboxylate A 5 L pressure tank reactor was charged with 5-bromo-6-methylpyrazin-2-amine (510 g, 2.71 mol, 1.00 equiv), triethylamine (830 g, 8.22 mol, 3.02 equiv), methanol (3.5 L) and Pd(dppf)Cl2 (60 g). The reactor was pressurized with CO gas (10 atm) and was stirred for 24 h at 70 C. The pressure was then released; and the resulting solid was filtered off. The filtrate was concentrated under vacuum. Water was added to the resulting residue and the mixture was extracted with ethyl acetate (6 x 1 L). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give the title compound, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-6-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COLLETTI, Steven, L.; DEMONG, Duane; DYKSTRA, Kevin, D.; HU, Zhiyong; MILLER, Michael; (104 pag.)WO2019/99315; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6705-33-5,Some common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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.

Powdered potassium hydroxide (3.4 g, 60 mmol) was added to a mixture of 2-chloro- L-FLUORO-4-NITROBENZENE (10.5 g, 60 mmol) AND PYRAZIN-2-YLMETHANOL (6.6 g, 60 mmol ; Maury G. et al. , Bull. Soc. Chem. Belg. 1982,91, 153). Tetrabutylammonium bromide (50 mg) was added and the mixture was heated AT 80C for one hour and cooled to room temperature. The residue was dissolved in dichloromethane, washed with water and dried over magnesium sulfate. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 5% ethyl acetate in dichloromethane) to give 2- [ (2-CHLORO-4- nitrophenyl) oxymethyl] pyrazine (6.4 g, 40%) as a yellow solid. NMR Spectrum: (CDC13) 5.41 (s, 2H), 7.14 (d, 1H), 8.18 (dd, 1H), 8. 35 (d, 1H), 8.61 (d, 2H), 8.94 (s, 1H).

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26151; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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: Acetylpyrazine

Bromine (0.23 mL, 4.49 mmol) was added over 3 min. to a ~80C solution of 2- acetylpyrazine (0.50 g, 4.09 mmol) in 48% HBr (10 mL). The resulting mixture was heated between 80-90C for 1h, concentrated then reconcentrated again from acetone. Trituration of the resulting red-brown solid with ether/acetone (20 mL/5 mL) gave 0.94 g (82%) of 2-bromo- 1-pyrazin-2-yl-ethanone as a hydrobromide salt which had: NMR (DMSOd6) 9.12 (d, 1.2 Hz, 1 H), 8.89 (d, J = 2.5 Hz, 1 H), 8.78 (dd, J = 2.5, 1.7 Hz, 1 H), 8.07 br s, 1H + residual water), 4.96 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22047-25-2, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 875781-43-4, A common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

2-Bromo-5H-pyrrolo[2,3-b]pyrazine SM-1 (500 mg, 2.5 mmol), 1-Boc-4-(methylamino)piperidine SM-5a (1.082 g, 5.0 mmol), Pd2(dba)3 (139 mg, 0.1 mmol), DavePhos (238 mg, 0.6 mmol) and LiHMDS (12.625 mL, 12 mmol) are taken-up in dry THF (10 mL) and the resulting mixture is flushed with Argon and stirred for 1 h at 80 C. The reaction mixture is diluted with H2O and AcCN, Isolute is added, the solvent is removed in vacuo and the residue is purified via RP HPLC. The product containing fractions of IM-1a (HPLC-MS method A: tRet.=1.72 min; MS (M+H)+=332) are freeze dried.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Stadtmueller, Heinz; US2013/29993; (2013); 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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 6-chloropyrazine-2-carboxylate

A mixture of 17 mmol methyl-5-chloropyrazine-2-carboxylate, 18 mmol of N-BOC-piperazine and 20 mmol of K2CO3 in 20 ml of acetonitrile was heated under reflux for 3 hours. The reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The title compound was recrystallized from ethyl acetate to yield a colorless solid. MS (m/e): 323.4 (MH+, 100%)

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; Jolidon, Synese J.; Narquizian, Robert; Nettekoven, Matthias Heinrich; Norcross, Roger David; Pinard, Emmanuel; Stalder, Henri; US2005/209241; (2005); 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 4430-75-5 as follows. Product Details of 4430-75-5

8. Synthesis of 2-(1-(triisopropylsityl)-1H-indol-6-yl)-octahydro-1H-pyrido[1,2-a]pyrazine Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 6-bromo-1-(triisopropylsilyl)-1H-indole (2 g, 5.40 mmol). To this was added octahydro-1H-pyrido[1,2-a]pyrazine (2.1 g, 14.25 mmol). Addition of t-BuONa (2 g, 20.83 mmol) was next. This was followed by the addition of (t-Bu)3P (200 mg, 0.99 mmol). This was followed by the addition of Pd(OAc)2 (50 mg, 0.22 mmol). To the mixture was added xylene (30 mL). The resulting solution was allowed to react, with stirring, for 2 hours while the temperature was maintained at 110 C. in a bath of oil. The reaction progress was monitored by TLC (CH2Cl2MeOH=10:1). The resulting mixture was washed 1 time with 30 mL of H2O. The resulting solution was extracted three times with 100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed 1 time with 10 mL of NaCl(sat.). The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 2.15 g (80%) of 2-(1-(triisopropylsilyl)-1H-indol-6-yl)-octahydro-1H-pyrido[1,2-a]pyrazine as red oil.

According to the analysis of related databases, 4430-75-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/200471; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54608-52-5, These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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.

(00646] Step A: 5-amino-4-methyl- 1 -(pyrazin-2-yl)- 1 H-pyrazol-3 (2H)-one: To a mixture of 2-hydrazinylpyrazine (0.551 g, 5.00 mmol) and ethyl 2-cyanopropanoate (0.669 g, 5.00 mmol) in abs. EtOH (10 mL) was added 3M NaOEt in EtOH (0.167 mL, 0.501 mmol) and the mixture was heated at reflux for 64 hours. The mixture was concentrated and the residual yellow-brown solid was treated with EtOAc (30 mL) and sonicated. The resulting tan suspension was stirred vigorously for 8 hours. The solid was collected via vacuum filtration, washed with EtOAc and dried in vacuum to afford the title compound as a light tan powder (682 mg, 7 1%). ?H NMR (DMSO d6) oe 10.3 (br s, 1H), 8.82 (s, 111), 8.30 (d, 211), 6.55 (s, 2H), 1.71 (s, 3H).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; ANDREWS, Steven Wade; BLAKE, James F.; BRANDHUBER, Barbara J.; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78325; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, Application In Synthesis of 2,6-Dichloropyrazine

To a solution of lithium diisopropylamide (2.0 M heptane/tetrahydrofuran/ethylbenzene, 11.10 mL, 22.20 mmol) in THF (75 mL) at -78 C was added a solution of 2,6-dichloropyrazine (1.44 g, 9.67 mmol) in THF (20 mL) at room temperature over 20 min. The reaction mixture was stirred at -78 C for 1.5 h and added via cannula to a 3 -neck flask containing dry ice at -78 C. The reaction mixture was warmed from -78 C to room temperature over 21 h and quenched with 5 M HC1. The mixture was partitioned between brine and EtOAc. The aqueous phase was acidified to pH 3.5 with 5 M HC1. The aqueous phase was extracted with EtOAc (6 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 10% MeOH in DCM) gave 3,5-dichloropyrazine-2-carboxylic acid (0.408 g, 2.11 mmol, 22% yield) as a light brown solid. LC/MS (ESf ) m/z = 193.0 (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; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem