Category: Pyrazines

Synthetic Route of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol) in THF (4.5 mL) at RT was added sodium hydride (60% wt. dispersion, 0.199 g, 4.98 mmol) and methanol (0.200 mL, 4.94 mmol). The reaction mixture was stirred at RT for 30 min, diluted with EtOAc, and quenched with saturated NH4C1. The reaction mixture was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc (3 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 (10% to 50% EtOAc in hexanes) gave ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol, 98% yield) as an off white solid. LC/MS (ESf ) m/z = 199.1 (M+H)+

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

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

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-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 69214-33-1, Safety of 8-Chloroimidazo[1,2-a]pyrazine

Intermediate Example 2-1 : Preparation of 3-bromo-8-chloro-imidazo[1 ,2- ajpyrazineTo a stirred solution of 8-chloro-imidazo[1 ,2-a]pyrazine (164.2 g g, 1070 mmol) in 950 mL DMF is added NBS (190.3 g, 1070 mmol) in one portion and the mixture is stirred overnight at rt. The mixture is poured on 9500 mL water, filterd and the residue is washed with water (2 x 1000 mL) and dried in vaccuo to yield 152.6 g (61.4 %) of the title compound. 1H-NMR (300 MHz, d6-DMSO): delta =8.45 (d, 1 H), 8.00 (s, 1 H), 7.83 (d, 1 H) ppm.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (2012); A1;,
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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

A mixture of 3,5-dibromo-l-methyl-2(lH)pyrazinone (2.0g;7.5mmol), 2-(4-Amino-phenyl)-ethanol (1.Og; 7.3mmol), and l-methyl-2- pyrrolidinone (ImL) was heated at 120 0C for lhr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown oil. This was dissolved in CH2Cl2 and washed with 0.0 IN NaOH, and dried over solid sodium sulfate. After filtration and evaporation of the CH2Cl2 layer, the resulting brown solid was chromatographed on silica using methanol/CH2Cl2 (1:9) as eluent to provide 2.0g of 5-bromo-3-[4-(2-hydroxy-ethyl)-phenylamino]-l-methyl-lH-pyrazin-2-one (1) as a light tan solid. MS 324.23 (M+H).

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 87486-34-8.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WHITNEY, James A.; DI PAOLO, Julie; VALLECA, Mark A.; BRITELLI, David R.; CURRIE, Kevin S.; DARROW, James W.; KROPF, Jeffrey E.; LEE, Tony; GALLION, Steven L.; MITCHELL, Scott A.; PIPPEN, Douglas A.I.; BLOMGREN, Peter A.; STAFFORD, Douglas Gregory; WO2008/33858; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 123-32-0, 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 123-32-0 as follows.

Example 5 BSc4352: 4,4′-(1E,1’E)-2,2′-(pyrazine-2,5-diyl)bis(ethene-2,1-diyl)bis(N,N-dimethylaniline) Synthesis: 2,5-Dimethylpyrazine (0.125 g, 1.16 mmol) is dissolved in 10 ml dimethylformamide, followed by addition of 4-(dimethylamino)benzaldehyde (0.345 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, 0.308 g (yield: 72%) of the product BSc4352 is obtained as red solid.1H-NMR (CDCl3, 500 MHz): delta=8.49 (s, 2H), 7.62 (d, J=16 Hz, 2H), 7.49 (d, J=8.9 Hz, 4H), 6.96 (d, J=16 Hz, 2H), 6.72 (d, J=8.9 Hz, 4H), 3.02 (s, 12H) ppm13C-NMR (CDCl3, 125 MHz): delta=149.7, 148.0, 141.7, 132.8, 127.5, 123.7, 118.7, 111.2, 39.3 ppm.

According to the analysis of related databases, 123-32-0, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-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.

2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65% (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93% (13.6 g; 94.07 mmol); HPLC-MS: (M+H)+=145/147; tRet=0.34 min; method FECB5.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; GIANNI, Davide; SMETHURST, Christian; US2014/142098; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 117719-17-2, 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. 117719-17-2 name is 5-Bromo-3-morpholinopyrazin-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.

A solution of 5-bromo-3-morpholinopyrazin-2-amine (0.200 g, 0.772 mmol) in DME (1.5 mL), 2-chlorocyclopentanone (0.1 6 mL, 1.158 mmol) was added. The mixture was heated at 120 C for 16 h, until the reactants were consumed as determined by LCMS analysis. The reaction mixtures were diluted with DCM (100 ml_) mixed, washed with saturated aqueous solution of NaHC03, brine, dried over Na2S04 and concentrated in vacuo. The dark residue was purified by biotage (cyclohex/EtOAc 1 :1) to obtain 30 mg of desired compound I-04 as a white solid, which was used in next reaction step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-3-morpholinopyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6705-33-5, 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. 6705-33-5 name is Pyrazin-2-ylmethanol, 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.

To a stirred solution pyrazin-2-ylmethanol (500 mg, 4.545 mmol) in DCM (20 ml) was added Dess-martin periodinane (2.89 g, 6.818 mmol) and stirred for 1 hr at RT. Reaction mass was diluted with DCM (100 ml) washed with saturated sodium bicarbonate solution (50 ml X 2) twice. DCM part was separated, dried over sodium sulfate, evaporated to dryness to get 300 mg crude, which was purified by column chromatography using 100-200 silica and 20% EtOAc in hexane as eluent to afford pyrazine-2-carbaldehyde (100 mg) as brown liquid.

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

Reference:
Patent; CURADEV PHARMA PVT. LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Veejendra K; KAPOOR, Kishore Kamal; WO2014/141110; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, HPLC of Formula: C5H7Cl2N3

N,N-diisopropylethylamine (109 mmol, 18.01 ml) and a solution of benzyl 3-(chlorocarbonyl)azetidine-1- carboxylate (5.53 g) in dichloromethane (32.5 ml) were added to a stirred suspension of 2-aminomethyl-3- chloropyrazine hydrochloride (content 77%; 21.80 mmol, 5.10 g) in dichloromethane (55 ml) at room temperature to give a dark brown solution. After stirring at room temperature for two hours the reaction mixture was quenched with water and filtered over decalite. Layers were separated and to the aqueous layer saturated aqueous sodium hydrogencarbonate solution was added and the layer was extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane / methanol gradient 10/0 to 9/1 ) to give benzyl 3-((3-chloropyrazin-2- yl)methylcarbamoyl)azetidine-1-carboxylate (6.46 g).NMR (CDCl3, 400 MHz): delta 3.37 -3.45 (m, 1 H), 4.16 – 4.30 (m, 4H), 4.71 (d, J = 5 Hz, 2H), 5.10 (s, 2H), 6.92 – 6.97 (m, 1 H), 7.28 – 7.47 (m, 5H), 8.33 (d, J = 2 Hz, 1 H), 8.44 (d, J = 2 Hz, 1 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; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 54608-52-5, A common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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.

441 mg (2.0 mmol) of the compound from Example 12A and 220 mg (2.0 mmol) of the compound from Example 3A are initially charged in 10 ml of ethanol. 93 mg (0.4 mmol) of camphor-10-sulfonic acid are added, and the mixture is stirred under reflux for 5 h. The mixture is allowed to cool to RT, and the solid formed is filtered off and washed once with a little ethanol. 10 ml of a 4 N solution of hydrogen chloride in dioxane are then added, and the mixture is stirred at RT for 30 min. The mixture is then concentrated on a rotary evaporator, and the residue is dried under high vacuum.Yield: 260 mg (47% of theory)LC-MS (Method 1): Rt=1.93 min; MS (ESIpos): m/z=240 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=9.70 (s, 1H), 9.43 (s, 1H), 9.08 (d, 1H), 9.01 (s, 1H), 8.70 (d, 1H), 8.61 (s, 2H), 8.08 (dd, 1H).

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

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5900-13-0,Some common heterocyclic compound, 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, molecular formula is C5H6BrN3O, 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.

Example 1: 4-[(5-Bromo-3-methoxypyrazin-2-yl)imino]-2,6-di-tert-butylcyclohexa-2,5- dien-l-one A1C13 (651 mg, 4.9 mmol) was added to a solution of pyridine (0.95 ml) and 1,2- dichloroethane (25 ml). The resulting mixture was refluxed for 15 min. 2,6-Di-tert-butyl- 1,4-benzoquinone (434 mg, 1.97 mmol) and 5-bromo-3-methoxypyrazin-2-amine (420 mg, 1.97 mmol) was added and the resulting mixture was refluxed for 18 h. After cooling to RT, the mixture was filtered through celite. Celite was washed with DCM and the combined organic phase was concentrated under reduced pressure. The product was purified using column chromatography. Yield: 80 mg 1H NMR (CDC13): 1.21 (9H, s), 1.30 (9H, s), 4.07 (3H, s), 6.90 (1H, m), 7.07 (1H, m), 8.10 (1H, s)

The synthetic route of 5900-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem