Pyrazines

Adding a certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-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 4858-85-9, category: Pyrazines

A mixture 2,3-dichloro-pyrazine (5.0 g, 34 mmol), 1-isopropylpiperazine (6.5 g, 51 mmol) and potassium carbonate (7.0 g, 51 mmol) in acetonitrile (100 mL) was stirred at ambient temperature for 2 h. Addition of hexane, followed by filtration and concentration of the filtrate gave 9.5 g of crude material as an orange liquid. Purification by filtration through silica using heptane/EtOAc (3: 1), followed by EtOAc/acetone (1: 1), provided 6.5 g (79%) of the title compound as a yellow oil which solidified upon cooling. HPLC purity: 98%. MS m/z 241 (M+H) +. HRMS m/z calcd for C11H17ClN4 (M) + 240.1142, found 240.1138.

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

Reference:
Patent; BIOVITRUM AB; WO2004/9586; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 21279-62-9, 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. 21279-62-9, name is 3-Chloropyrazine-2-carboxamide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.

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, 3-Chloropyrazine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 113305-94-5, The chemical industry reduces the impact on the environment during synthesis 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

Reflux a solution of 2.24 g (18.65 mmol) of 5-aminopyrazine-2-carbonitrile and 9.45 mL (74.40 mmol) of boron trifluoride etherate in 50 mL of methanol for 2 h. Concentrate the reaction mixture under reduced pressure and take up the residue obtained in 200 mL of EtOAc and 10 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluding with a cyclohexane/EtOAc 1:1 mixture. After concentration under reduced pressure, we obtain 1.4 g of methyl 5-aminopyrazine-2-carboxylate in the form of oil. Yield=49%

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, 5-Aminopyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 121246-96-6, 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. 121246-96-6 name is 3-Chloropyrazine-2-carbaldehyde, 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.

Preparation 1; 4-Methyi-3,4,5,6-tetrahydro-2H-[1,2’lbip(at)rrazinyl-3′-carbaldehyde; n-BuLi (56 mmol, 22.4 mL, 2.5 M in hexanes) was added to tetrahydrofuran (300 mL) cooled to-78 C followed by the addition of 2,2-6,6-tetramethylpiperidine (52 mmol, 8.71 mL). The solution was removed from the cooling bath and stirred for 30 minutes and then cooled back to -78C. 2-chloropyrazine (40 mmol, 3.65 mL) was added dropwise, and the solution turned a reddish-brown color. After stirring 30 minutes, methylformate (60 mmol, 3.7 mL) was added and the reaction mixture was stirred for 2.25 hrs at -78C. Acetic acid (8 mL) was added and the mixture was warmed to 0C, was washed 3 times with 1: 1 brine-water, dried over sodium sulfate, and then concentrated in vacuo. The residue was dissolved in 1,4- dioxane (250 mL) and 1-methylpiperazine (60 mmol, 6.6mL) and potassium carbonate solution (8.28g in 60 mL of water) were added and the mixture was heated at 100C for 1.5 hours. After cooling to room temperature, the mixture was filtered through a Celite pad which was then washed with chloroform. The filtrate was concentrated in vacuo and purified by silica gel chromatography (100: 1:1 chloroform-methanol-ammonium hydroxide) to yield 3.3 g (40% yield for two steps) of 4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-carbaldehyde; ¹3C NMR (100 MHz, CDC13) d 191.7,154.3, 145.3,134.5, 133.2, 55.1, 48.7, 46.3; MS (AP/CI) 207.2 (M+H)+.

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/113535; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate C75-Chloro-3-( I ,3-dimethyl-I H-pyrazol-4-yl)-pyrazi n-2-ylam me To a solution of 3-bromo-5-chloropyrazin-2-amine (3.75 g, 18.01 mmol) in DME (90 mL) wasadded 1 ,3-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (4 g, 18.01 mmol), bis(triphenylphosphine)palladium(ll) chloride (0.632 g, 0.901 mmol) and Na2003 (aq.2.OM) (27.0 mL, 54.0 mmol). The reaction was heated to 90C overnight. The reaction was added to water (250m1) and the product was extracted into EtOAc (2 x 230m1). The organic phase was washed with brine, dried over MgSO4. The solids were removed by filtration, washed with EtOAc and the filtrate concentrated under vacuum. The crude product was purified by flash column chromatography, eluting with 0-10% gradient of (2M NH3 in MeOH)in DCM on a 80g Si-column, loading with DCM to give the product (2.5g)LCMS: Rt 0.81 mins; MS mlz 224.0 [M+H]+; Method 2minLowpHvol

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-chloropyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); 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. 61655-72-9, name is 6-Chloro-N,N-dimethylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Chloro-N,N-dimethylpyrazin-2-amine

B. 2-(2-Dimethylaminoethylamino)-6-dimethylaminopyrazine. Following the process of Example 3A using 2-chloro-6-dimethylaminopyrazine there is obtained, 2-(2-dimethylaminoethylamino)-6-dimethylaminopyrazine.

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 61655-72-9.

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

Related Products of 98-97-5, 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. 98-97-5, name is Pyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(a) A mixture of 68.2 g (0.55 moles) 2-pyrazine carboxylic acid and methylene chloride (about 200 ml) containing a catalytic amount of pyridine was warmed (to about 30 C.). To that mixture, 78.5 g (0.66 mole) thionyl chloride was added dropwise. The reaction mixture was refluxed for 24 hours. The methylene chloride was removed under reduced pressure and heat to give the 2-pyrazine carboxylic acid chloride which was used in step (b) without further isolation.

The synthetic route of Pyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chevron Research Company; US4732894; (1988); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

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

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1, 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 36070-80-1 as follows.

[00778] To a solution of lenalidomide (0.2g, 0.77 mmol) in DMF (4 mL) was added 5-chloropyrazine-2-carboxylic acid (0.15g, 0.95 mmol), HATU, (0.29g, 0.77 mmol), and DIPEA (0.27mL, 1.54 mmol). The reaction was stirred at room temperature for 1 hr before it was quenched with saturated NH4C1 (5 mL). The mixture was extracted with EtOAc (10 mLx3), and the combined organic phase was dried over Na2SO4 and concentrated. Column chromatography gave 5-chloro-N-(2- (2,6-dioxopiperidin-3-yl)- 1 -oxoisoindolin-4-yl)pyrazine-2-carboxamide (0.1 g, 33%).

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHIMMANAMADA, Dinesh, U.; YING, Weiwen; WO2013/158644; (2013); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem