Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, 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 58139-04-1, COA of Formula: C5H5IN2O

Step 1: tert-Butyl (1-(4-((3-methoxypyrazin-2-yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 2-iodo-3-methoxypyrazine (163 mg, 0.69 mmol) intriethylamine (1.5 mL) at 0 C was added Pd(P’Bu3)2 (14.1 mg, 6 mol%), Cul (1.8 mg, 2 mol%) and fert-butyl (1 -(4-ethynylphenyl)cyclobutyl)carbamate (125 mg, 0.46 mmol). The brown suspension was stirred for 6 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0 to 25% EtOAc in hexane) to give the title compound as a white solid (124 mg, 47%). 1H-NMR (500 MHz, CDCI3) delta 8.15 (s, 1 H), 8.04 (s, 1 H), 7.60 (d, 2H), 7.44 (d, 1 H), 5.30 (bs, 1 H), 4.1 1 (s, 3H), 2.51 -2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.91 (m, 1 H), 1.37 (bs, 9H).

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-Iodo-3-methoxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H16N2O2

A 5 L- 3 necked round bottomed flask, equipped with a mechanical stirrer, temperature probe, addition funnel and N2 inlet, was charged with the Schollkopf chiral auxiliary-(Int-13a, 200 g, 1.09 mol, 1.0 eq), bis(chloromethyl) dimethylsilane (Int-13b, 256 g, 1.63 mol, 1.5 eq), and THF (2 L, Aldrich anhydrous). The flask was cooled in a dry ice/ 2-propanol bath until the internal temperature reached -75 °C. n-Butyllithium (Aldrich 2.5 M in hexanes , 478 mL, 1.19 mol, 1.09 eq) was added via a dropping funnel over 1 hour while maintaining the internal reaction temperature between -67 °C and – 76 °C. The resulting orange-red solution was allowed to gradually warm to room temperature for about 15 hours. The reaction mixture was then re-cooled to 0 °C and quenched with 500 mL of water. Diethyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 1 L of diethyl ether. The combined organic extracts was washed with water and brine, dried with MgSC^, filtered, and concentrated in vacuo, giving 480 g of orange oil. This material was left in vacuo for about 15 hours to provide 420 g of oil. The crude product was split into two batches and purified via silica gel chromatography on a 1.6 kg flash column. The column was eluted with gradient of 0-4percent Epsilon20 in hexanes. The product fractions were concentrated in vacuo at a bath temperature at or below 40 °C giving 190 grams of Int-13c-(60percentyield).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 75907-74-3,Some common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, molecular formula is C8H12N2O, 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.

A suspension of 3,5,6-trimethylpyrazine-2-yl)methanol (see Bioorg. Med. Chem. 2007, 15, 3315; 14.8 g, 97.2 mmol) and manganes(IV) oxide (30.0 g) in dichloromethane was stirred at room temperature for 3 days. The reaction mixture was filtrated through Celite with dichloromethane. The filtrate was combined and concentrated in vacuo to give 3,5,6-trimethylpyrazine-2-carbardehyde. MS (APCI): m/z 151 (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 (3,5,6-Trimethylpyrazin-2-yl)methanol, its application will become more common.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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: Methyl 5-chloropyrazine-2-carboxylate

Example 190C methyl 5-ethenylpyrazine-2-carboxylate (1430) A solution of methyl 5-chloropyrazine-2-carboxylate (3 g, 17.38 mmol), potassium vinyltrifluoroborate (5.12 g, 38.2 mmol) and 1,1?-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (1.272 g, 1.738 mmol) in isopropyl alcohol (45 mL, anhydrous) was treated with triethylamine (4.85 mL, 34.8 mmol) and the atmosphere was vacuum purged with N2 a few times. The mixture was heated at 80 C. under N2 for 2 hours and cooled. The mixture was partitoned between saturated aqueous NaHCO3 solution (50 mL) and ethyl acetate (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with a gradient of 25 to 100% ethyl acetate in heptanes to provide the title compound (2.28 g, 13.89 mmol, 80% yield)1H NMR (400 MHz, CDCl3) delta 9.23 (d, J=1.0 Hz, 1H), 8.67 (d, J=1.1 Hz, 1H), 6.89 (dd, J=17.4, 10.8 Hz, 1H), 6.51 (d, J=17.4 Hz, 1H), 5.78 (d, J=10.9 Hz, 1H), 4.03 (s, 3H); LC/MS (ESI+) m/z 165 (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 33332-25-1, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1458-18-0

a) 3-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl esterTo a mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [CAS 1458-18-0] and 3-amino-6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester [CAS 14340-25-1] (799 mg, 3 mmol) in DMF was added 2-methoxy-ethylamine (0.31 ml, 3.6 mmol) and NEt3 (2.09 ml, 15 mmol) and the mixture was stirred at r.t. for 3.5 h. The reaction mixture was poured into water (150 ml) and extracted with toluene (2×150 ml). The organic layers were washed with half-saturated aq. sodium chloride, combined, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%) to provide the title compound together with 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (about 1:1) as colorless solid. This mixture was used for the next step.HPLC: RtH4=0.77 min; ESIMS [M+H]+=305.1; (Cl-pyrazine: HPLC: RtH4=0.73 min; ESIMS [M+H]+=261.1).

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 1458-18-0.

Reference:
Patent; BADIGER, Sangamesh; CHEBROLU, Murali; HURTH, Konstanze; JACQUIER, Sebastien; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; US2012/184539; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (0.444 g, 2.0 mmol) in tetrahydrofuran (5 mL)/water (10 mL)/toluene (20 mL) was added phenyl boronic acid (0.536 g, 4.4 mmol), sodium carbonate (0.699 g, 6.6 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.116 g, 0.10 mmol). The reaction was evacuated and purged with nitrogen several times before being refluxed for 6 h. The organic layer was separated and the aqueous layer extracted with toluene (3 x 20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give methyl 3-amino-6-chloro-5-phenyl-2-pyrazinecarboxylate as a yellow solid (0.43 g, 82%).

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

Reference:
Patent; Biotron Limited; Gage, Peter William; Ewart, Gary Dinneen; Wilson, Lauren Elizabeth; Best, Wayne; Premkumar, Anita; US2015/313909; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14399-37-2, 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. 14399-37-2, name is 3,6-Dichloropyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a 200 mL round bottom flask was added Na2S (10.816 g, 44wt% containing crystalline water, 60.978mmol) and toluene (100 mL). The mixture was heated to reflux, and water was removed with a Dean-Stark trap (about 5~6 mL water was distilled out). After cooling, the mixture was concentrated to dry.To above round bottom flask was added Y7d (5.000 g, 30.489mmol) and 2-methylbutan-2-ol (50 mL), the reaction was heated to reflux and stirred for 36 h. After cooling to 25 C, the mixture was filtered. The solvent of the filtrate was exchanged with n-heptane (5 V*3 times, based on Y7d), and finally concentrated to IV residue. THF (25 mL) was charged to the residue at 25 C and stirred. The suspension was filtered and washed with THF/n-heptane (5 mL/5 mL) to give a brown solid (6.200 g).To another 200 mL round bottom flask was added above brown solid (6.200 g),10% brine (25 mL), Me-THF (30 mL) and n-BmNBr (9.829 g, 30.489 mmol). The mixture was stirred for 0.5 h at room temperature, and the phases were separated. The organic phase was washed with 20% brine (25 mL), and exchanged the solvent with /.vo-propanol (5 V *3 times, based on Y7d) to give the /.vo-propanol solution of Y7c (27.000g, 99.2% purity by HPLC area, 58.08% assay yield). 1H NMR (400 MHz, DMSO-d6) d = 6.88 (s, 1H), 2.97 – 2.92 (m, 14H),1.38 – 1.31 (m, 14H), 1.13 – 1.04 (m, 14H), 0.73 – 0.69 (t, 21H). The advantage of the use of n- Bu4NBr (or other corresponding tert-alkylaminohalogenide) is easier workup and purification.

The synthetic route of 3,6-Dichloropyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); 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. 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-Aminopyrazine-2-carboxylic acid

15 g of 3-aminopyrazine-2-carboxylic acid was added to 200 ml of methanol.Add 10 ml of thionyl chloride, stir overnight at room temperature, and concentrate.200 ml of toluene was added and concentrated to give 18 g of 3-aminopyrazine-2-carboxylic acid methyl ester.

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; Changsha Shencheng Biological Technology Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107513041; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 4-[3-(5-Methyl-pyrazin-2-yl)-ureido]-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester. To a stirred, cooled (about 0 C.) solution of 4-amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (258 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (139 muL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, 5-methyl-2-amino pyrazine (109 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. The reaction was allowed to cool to room temperature, then diluted with ethyl acetate (50 mL) and water (50 mL). A precipitate formed which was filtered and dried under reduced pressure to yield the desired material as a white solid (47% yield). 1H-NMR (400 MHz, d6-DMSO) delta10.29 (s, 1H), 8.79 (s, 1H), 8.68 (d, 1H, 8.59 (br s, 1H), 8.48 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.51 (m, 1H), 5.32 (s, 2H), 3.88 (s, 3H), 2.32 (s, 3H).

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

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); 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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H6N4

General procedure: To a stirred solution of2-hydrazinopyridines 1a-k or 2-hydrazinopyrazines 2a-f (1equiv.) and aldehyde 3a-k (1equiv.) in polyethyleneglycol (PEG) (10 mL) were added p-TsOH (5 mol%)) and DDQ (2 equiv.). The mixture was stirred at reflux untilthe starting material was completely consumed (monitored by TLC, 1h) and then cooled down to roomtemperature. After filtration and evaporation of solvent from the filtrate, the resulting residue was purified bysilica gel column chromatography (EtOAc/Hexane, 3:7 v/v), affording the pure N-fused 1,2,4-triazolederivative, [1,2,4]triazolo[4,3-a]pyridines 4a-k & [1,2,4]triazolo[4,3-a]pyrazines 5a-f.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bhatt, Ashish; Singh, Rajesh K.; Kant, Ravi; Arkivoc; vol. 2018; 7; (2018); p. 236 – 247;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem