Category: Pyrazines

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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
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 486460-21-3 as follows. Product Details of 486460-21-3

To a stirring mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine (5.00 g, 26.0 mmol) and sodium tungstate dihydrate (0.343 g, 1.04 mmol) in water (5 mL) at 0 C was added 30% hydrogen peroxide soln (6.1 mL) dropwise over 15 min. The reaction was warmed to rt, kept at rt for 5 min, then cooled again over an ice bath. After 20 min sodium bisulfite (lg) was added portionwise followed by CH2CI2 (300 mL), MeOH (30 mL) and NaCl to saturate the mixture. After stirring for 16h the solids were allowed to settle and the liquids were decanted away. The solids were washed with 10% MeOH/CH2Cl2. The organics were combined, dried with Na2S04, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Si02, 0-10% (10% 2N NH3/MeOH)/DCM) to obtain the product as a yellow oil (5.36 g, 26%).

According to the analysis of related databases, 486460-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANDRES GIL, JOSE IGNACIO; LETAVIC, MICHAEL A; RECH, JASON C; RUDOLPH, DALE A; SOYODE-JOHNSON, AKINOLA; CHROVIAN, CHRISTA C; (158 pag.)JP2017/527588; (2017); A;,
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. 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8N2O2

a) 3-Methyl-4-oxy-pyrazine-2-carboxylic acid methyl ester To a solution of 2.0 g (13.14 mmol) 3-methyl-pyrazine-2-carboxylic acid methyl ester in 40 ml CHCl3 was added 3.24 g (13.14 mmol) meta-chlorperoxybenzoic acid and the resulting mixture was heated to reflux for 1.5 h. The reaction mixture was basified with saturated aqueous NaHCO3 and extraced with CHCl3, the combined organic layers were dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (DCM to DCM/MeOH 9:1) to provide the title compound as colorless solid. HPLC: RtH11=0.40 min; ESIMS [M+H]+=169; 1H NMR (600 MHz, DMSO-d6): 8.56 (d, 1H), 8.48 (d, 1H), 3.33 (s, 3H).

The synthetic route of 41110-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US8338413; (2012); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 93049-39-9, 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. 93049-39-9, name is 7-Chloropyrido[3,4-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 383-(Pyridor3,4-&1pyrazin-7-ylN)benzaldehyde 7-Chloropyrido[3,4-Z?]pyrazine (140 mg, 0.85 mmol), 3-formylbenzeneboronic acid (127 mg, 0.85 mmol), potassium phosphate (180 mg, 0.85 mmol), water (2 mL), DME (6 mL) and Pd(PPh3)4 (100 mg, 0.085 mmol) were combined in a sealed tube and heated under microwave irradiation to 1400C for 30 minutes. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated to dryness to give the title compound (155 mg, 77%) as an off-white solid. deltaH (DMSOd6) 10.21 (IH, s), 9.69 (IH, s), 9.26 (IH, d, J 1.82 Hz), 9.15 (IH, d, J 1.83 Hz), 8.93 (IH, s), 8.76 (IH, s), 8.70 (IH, d, J 7.80 Hz), 8.07 (IH, d, J 7.61 Hz), 7.84 (lH, t, J7.68 Hz).

The chemical industry reduces the impact on the environment during synthesis 7-Chloropyrido[3,4-b]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25710-18-3, A common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, molecular formula is C7H3Cl2N3, 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: A mixture of 2,3-dichloropyrazine or its derivatives (1, 1.0 equiv), substituted phenols (2a-p) (1.0 equiv) and anhydrous AlCl3 (1.0 equiv) in dichloroethane (5 mL) was stirred at 80 oC for 30 min. Then the mixture was cooled to room temperature and additional quantity of AlCl3 (1.0 equiv) was added. The mixture was stirred again at 80 oC for another 30 min. After completion of the reaction, the mixture was poured into ice-cold water (15 mL), stirred for 10 min and then extracted with ethyl acetate (3.x.5 mL). The organic layers were collected, combined, washed with water (3.x.10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to afford the expected products.

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, K. Shiva; Adepu, Raju; Kapavarapu, Ravikumar; Rambabu; Krishna, G. Rama; Reddy, C. Malla; Priya, K. Krishna; Parsa, Kishore V.L.; Pal, Manojit; Tetrahedron Letters; vol. 53; 9; (2012); p. 1134 – 1138;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 939412-86-9, 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. 939412-86-9 name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 solution of (3R,8aR)-6-oxohexahydro-lH-pyrrolo[2,l-c][l,4]oxazine-3- carboxylic acid (600 mg, 3.24 mmoL ) in DCM ( 20 mL) was added isobutyl carbonochloridate (531 mg, 3.56 mmol) and TEA (0.53 mL, 3.78 mmol), the mixture was stirred at 0C for 1 hour, then (3-chloropyrazin-2-yl)methanamine hydrochloride (641 mg, 3.56 mmol) and TEA (1.1 mL, 7.56 mmol) was added at 0C. The mixture was stirred at 25C for 3 hours. To the mixture was added water (20 mL) and DCM (50 mL), the mixture was then separated and the aqueous layer was extracted with DCM (50 mL x 3), the combined organic layers were washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product, which was purified on silica gel column chromatograph (MeOH / DCM =0 ~ 10%) to give (3R,8aR)-N-((3- chloropyrazin-2-yl)methyl)-6-oxohexahydro- 1 H-pyrrolo [2, 1 -c] [ 1 ,4]oxazine-3 – carboxamide (300 mg, yield 29.8%) as a sheer oil. 1H NMR (400MHz, CHLOROFORM-d) d = 8.50 (d, J=2.5 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 7.78 (br. s., 1H), 4.74 (d, J=5.0 Hz, 2H), 4.52 (dd, J=3.1 , 13.4 Hz, 1H), 4.23 (dd, J=3.8, 1 1.3 Hz, 1H), 3.97 (dd, J=3.0, 1 1.0 Hz, 1H), 3.75 (dtd, J=4.0, 7.3, 10.8 Hz, 1H), 3.30 (t, J=1 1.0 Hz, 1H), 2.86 (t, J=12.3 Hz, 1H), 2.60 – 2.43 (m, 2H), 2.29 – 2.13 (m, 1H), 1.70 – 1.54 (m, 1H)

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 2-amino-6-(tri-n-butylstannyl)pyrazine (Example of the general procedure Tin-04, below): To a sealed tube, 2-amino-6-chloro-pyrazine (1 g), bis(tri-butyltin) (3.92 mL) and tetrakis-triphenylphosphine palladium, Pd(Ph3P)4 (100 mg) were combined in dioxane (10 mL). The reaction was heated at 110-120° C. for 10 h. After the mixture cooled down to room temperature, it was poured into 20 mL of water. The solution was extracted with EtOAc (4.x.20 mL). The combined extract was concentrated in vacuo to give a residue which was purified by silica gel chromatography to afford 2-amino-6-(tri-n-butylstannyl)pyrazine (0.5 g)

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-chloropyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); 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. 274-79-3, name is Imidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: Imidazo[1,2-a]pyrazine

Imidazo[1,2-a]pyrazine (7.2 g, 60.44 mmol) was dissolved in 2-methoxyethanol (100 ml). Platinum(IV) oxide (1.2 g, 5.13 mmol) was added, and the mixture was stirred overnight at room temperature, under a hydrogen atmosphere of 4 bar, in an autoclave. The reaction mixture was flooded with nitrogen, filtered over Celite, concentrated and coevaporated with toluene. Purification was carried out by column chromatography dichloromethane/7 N ammonia in methanol 95:5). Yield: 5.7 g (76%)

The synthetic route of 274-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2008/153843; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3, Recommanded Product: 313339-92-3

To a solution of N-{8-azabicyclo[3.2.1]octan-2-yl}-4-cyclopropylbenzamide hydrochloride (1.68 g, 4.73 mmol) in DMF (15 mL) DIPEA (3.3 mL, 18.9 mmol), and 3,5- dichloropyrazine-2-carbonitrile (0.93 g, 5.2 mmol) were added. The mixture was stirred at room temperature for 2h then it was partitioned between ethyl acetate and H2O. The combined organic phases were dried over Na2SO4, and evaporated to dryness to give N-[8-(6-chloro-5- cyanopyrazin-2-yl)-8-azabicyclo[3.2.1]octan-2-yl]-4-cyclopropylbenzamide (2.0 g, quant. yield) as an orange solid. MS found for C22H22ClN5O as (M+H)+ 408.0, 410.0.

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; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, The chemical industry reduces the impact on the environment during synthesis 33332-28-4, name is 2-Amino-6-chloropyrazine, I believe this compound will play a more active role in future production and life.

Intermediate 1 : 6-Methyl-2-pyrazinamine ; Dimethyl zinc (15.44 ml, 30.9 mmol) was added to a solution of 6-chloro-2- pyrazinamine (2 g, 15.44 mmol) and NiCI2(dppp) (0.837 g, 1.544 mmol) in dry 1 ,4- dioxane (75 ml) and the mixture was refluxed for 24 hours. The mixture was then cooled to room temperature, quenched with methanol and concentrated in vacuum. The residue was partitioned between EtOAc and brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated. The residue was purified by silica chromatography (MeOH-NH3-DCM) to afford the title compound as a pale yellow 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-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/115486; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem