Month: July 2021

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. Formula: C5H6N2O

Di-tert-butylazadicarboxylate (272 mg, 1.2 mmol) and pyrazin-2-ylmethanol (130 mg, 1.2 mmol) were added successively to an ice-cooled mixture of 2-methoxy-4-nitrophenol (200 mg, 1.2 mmol) and triphenylphosphine (310 mg, 1.2 mmol) in dichloromethane (6 ml). The mixture was stirred at room temperature for 1 hour. After evaporation of the solvent under vacuum, the residue was purified by chromatography on silica gel (eluant: 10%: 10% up to 40% : 40% ethyl acetate-dichloromethane in petroleum ether) to give 2- [ (2-methoxy-4- nitrophenoxy) methyl] pyrazine containing triphenylphosphine oxide (282 mg) : Mass spectrum : MH+ 262

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6705-33-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26151; (2005); 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H2BrIN2

EXAMPLE 50A (exo)-3-(5-Iodo-pyrazin-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane Under N2, the mixture of product from 7C (0.42 g, 3.0 mmol) was treated with potassium t-butoxide (Aldrich, 0.32 g, 3.3 mmol) in THF (anhydrous, Aldrich, 50 mL) at ambient temperature for 1 hours. The product of Example 41B (1.00 g, 3.5 mmol) and was added. The mixture was stirred at ambient temperature for 4 hours and quenched with water (5 mL). The mixture was concentrated and the residue was purified by chromatography (150 g SiO2, EtOAc:MeOH:NH3.H2O, 90:10:1, Rf. 0.40) to provide the title compound. 1H NMR (300 MHz, CD3OD) delta 1.90-2.25 (m, 4H), 2.31-2.60 (m, 4H), 2.84 (s, 3H), 3.94-4.11 (m, 2H), 5.32-5.57 (m, 1H), 8.06 (d, J=1.36 Hz, 1H), 8.42 (d, J=1.36 Hz, 1H) ppm; MS (DCI/NH3) m/z 346 (M+H)+.

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-01-1, 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

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.

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 3,5-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

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

Application of 16298-03-6, A common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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.

In fitted with magnetic stirring and reflux condensation tube (with drying tail pipe) 250 ml three-necked bottle are respectively added with a 3 – amino pyrazine -2 – carboxylic acid methyl ester 15.4g (about 0.1 muM), 120 ml of concentrated ammonia water, stirring at room temperature under the condition of 10h, filtering, washing, 60 °C drying, be 12.5g yellow solid that 3 – amino pyrazine -2 – formamide. Yield: 90.6

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; Li Zhulai; (15 pag.)CN106699759; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-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 486460-21-3, Application In Synthesis of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

Potassium tert-butoxide (2.24 g, 20 mmol) was dissolved in 40 mL of tetrahydrofuran in a 100 mL single-necked flask.Stir at room temperature for one minute. Then compound III (1.91 g, 10 mmol) was added in sequence.Compound II (2.60 g, 10 mmol) was stirred at room temperature for 60 min.Thereafter, the reaction solvent tetrahydrofuran was distilled off under reduced pressure, and then 50 mL of water and 50 mL of dichloromethane were added.The organic phase was extracted and the organic phase was dried with anhydrous sodium sulfate and evaporatedThe crude product was recrystallized from dichloromethane and cyclohexane to give 3.33 g of Compound IV.The yield was 82% and the purity was 99%.

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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anqing Qichuang Pharmaceutical Co., Ltd.; Wu Xueping; Xing Jigang; Yan Dongyang; Chen Yao; (11 pag.)CN108178761; (2018); A;,
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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H7F3N4

To a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[ 1 ,2,4] triazolo[4,3-a]pyrazine ( 1.90 g) in DMF ( 10 mL) was added 2C03 (2.35 g) and l -bromo-3-chloropropane (1.70 mL) at rt. The reaction mixture was heated at 80 C for 3 h, diluted with water and extracted with ethyl acetate. The combined organic phases were dried over anhydrous Na2S04 for lh, and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 30: 1 (v/v) DCM/MeOH) to give the title compound as transparent liquid (0.68 g, 30.00 %).

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5049-61-6, A common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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.

Description 4 5-Chloro-2-pyrazinamine (D4); Aminopyrazine (10 g, 105 mmol) was dissolved in dimethylformamide (60 ml) and N- chlorosuccinimide (15.36 g, 115 mmol) was added portionwise under argon at room temperature. After 5 minutes, the temperature rose from 25C to 45C (care required – exothermic reaction). An ice bath was placed underneath the reaction mixture and the mixture was stirred for 30 minutes and then allowed to warm to room temperature. The mixture was poured onto water and extracted with diethyl ether (x 5). The diethyl ether layer was evaporated under reduced pressure. The product was purified by Biotage column chromatography eluting with 10% ethyl acetate in pentane to afford the title compound (1.40 g). ¹H NMR (CDCI3) 8.02 (1 H, s), 7.76 (1 H, s), 4.61 (2H, s).

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/123723; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4744-50-7, 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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 3-(2-Phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-pyrazine-2-carboxylic acid Furo[3,4-b]pyrazine-5,7-dione (736 mg, 4.9 mmol) and DMAP (58 mg, cat.) were added to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 1.00 g, 4.8 mmol) in DMF (25 ml). The mixture was heated to 78 C. overnight, and cooled to RT. The formed precipitate was collected by filtration, and residual solvent was removed under vacuum. The thus obtained crude product (800 mg, 47%) was used in the next step without further purification. MS (m/e)=361.3 [M+H+].

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, 2,3-Pyrazinecarboxylic anhydride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alvarez Sanchez, Ruben; Bleicher, Konrad; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Rudolph, Markus; US2011/237564; (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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., Product Details of 59489-71-3

To the stirring solution of 2 (50 g, 287 mmol) in 1, 4-dioxane (1250 mL) was added 4- methoxycarbonyl phenyl boronic acid (2a) (56.89 g, 316 mmol) followed by 1M aqueous solution of potassium carbonate (575 mL, 574 mmol) at RT and purged with N2 gas for 40 minutes. Bis(triphenylphosphine)palladium(II)chloride (14.12 g, 20.12 mmol was added to the reaction mixture. The reaction mixture was heated to reflux temperature for 4h. After completion of the reaction (Confirm by TLC) the reaction mixture was cooled to RT and filtered through a bed of celite. The bed was washed with ethyl acetate (3 X 300 mL). Organic layer was separated and aqueous layer was re extracted with ethyl acetate (2 X 400 mL). The combined organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The crude material was purified by column chromatography over silica gel (230-400 mesh) using 3.5% of MeOH in DCM as an eluent to afford 3 (39.1 g, 57%) as yellow solid.

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27825-20-3,Some common heterocyclic compound, 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, molecular formula is C6H6N2O3, 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.

(1) 308 g (2 mol, 1 eq) of methyl 3-hydroxy-2-pyrazinecarboxylate and 956 g (6 mol, 3 eq) of liquid bromine were added to 4 L of acetonitrile,The mixture was stirred at 27 C for one hour,TLC detection reaction completely,The reaction solution was poured into 4 L of water,The excess liquid bromine was removed with a saturated aqueous solution of sodium sulfite,Standing filter,Filter cake vacuum drying at room temperature,300 g of the product methyl 6-bromo-3-hydroxy-2-pyrazinecarboxylate (including its tautomer 6-bromo-3-oxo-3,4-dihydro-2-pyrazinecarboxylic acid Methyl ester),Yield 65%.

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-Hydroxy-2-pyrazinecarboxylate, its application will become more common.

Reference:
Patent; Qingdao Hangdao District Chinese Medicine Hospital; Lu, Yanmin; (5 pag.)CN105732524; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem