Month: August 2021

Application of 50866-30-3, 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. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

To the starting material 5-methylpyrazine-2-carbaldehyde (100 mg, 0.8 mmol), THF (1.0mL) was added followed by phosphorene 8 (250 mg 1.7 mmol) at room temperature. Thereaction mixture was stirred for 8 h at 60 C. TLC revealed complete consumption ofstarting material. The reaction mixture was removed from heating bath and quenchedusing a saturated aqueous NH4Cl solution. Water (10 mL) and ethyl acetate (25 mL) wereadded, layers were separated washed with brine solution, dried over sodium sulfate andevaporated under reduced pressure to dryness. Then column purification was done to getthe pure product which was characterized by NMR. Yield: 72%

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

Reference:
Article; Balasubramaniam, Sivaraman; Vijayan, Sajith; Goldman, Liam V.; May, Xavier A.; Dodson, Kyra; Adhikari, Sweta; Rivas, Fatima; Watkins, Davita L.; Stoddard, Shana V.; Beilstein Journal of Organic Chemistry; vol. 16; (2020); p. 628 – 637;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, 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 87597-21-5, Application In Synthesis of Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

To a stirred solution of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate (13.95 g, 40 mmol) in toluene (558 mL) at 0 C. was added 80 mL DIBAH (120 mmol, 3 eq, 1.5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2%) (6,8-dibromoimidazo[1,2-a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta=8.93 (s, 1H), 8.05 (s, 1H), 5.46 (bs, 1H), 4.63 (s, 2H) ppm. UPLC-MS: RT=0.73 min; m/z 308.0 [MH+]; required MW=307.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Koppitz, Marcus; Klar, Ulrich; Jautelat, Rolf; Kosemund, Dirk; Bohlmann, Rolf; Bader, Benjamin; Lienau, Philip; Siemeister, Gerhard; US2013/267527; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1458-01-1, its application will become more common.

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

Synthetic Route of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

The reaction is carried out, under nitrogen, in a 1 L×4 neck flask equipped with a mechanical stirrer, water condenser (with gas inlet), and a thermocouple. The reactor is charged with 5-methylpyrazinecarboxylic acid (100 g), ethanol (300 g) and sulfuric acid (2 g). The contents are refluxed for eight hours at 78 C. The reaction mixture is cooled to ambient temperature and sodium bicarbonate (4 g) is added. About 75% of the solvent is removed under reduced pressure and the resulting suspension is allowed to stand overnight. The solids are filtered and washed with cold methanol (2×80 g). Drying under oven (25 inches of Hg) yielded 101.25 g (84%) of 5-methyl-2-pyrazonecarboxylic acid, ethyl ester.

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

Reference:
Patent; ISP INVESTMENTS INC.; US2005/261312; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, 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. category: Pyrazines

EXAMPLE 1A 5-bromo-2-pyrazinamine A 0 C. solution of 2-aminopyrazine (15.0 g, 157 mmol) in dichloromethane (900 mL) was treated with N-bromosuccinimide (28.2 g, 159 mmol), stirred for 3.5 hours, and filtered through diatomaceous earth (Celite). The filtrate was treated with silica gel (300 g) and concentrated. The concentrate was purified by flash column chromatography with 30% ethyl acetate/hexanes to provide 22.09 g (81.5%) of the desired product. MS (APCI(+)) m/z 174 (M+H)+; 1H NMR(300 MHz, CDCl3) delta 8.09 (d, J=1.4 Hz, 1H), 7.77 (d, J=1.7 Hz, 1H), 4.30-4.78 (br s, 2H).

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

Reference:
Patent; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 274-79-3,Some common heterocyclic compound, 274-79-3, name is Imidazo[1,2-a]pyrazine, molecular formula is C6H5N3, 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.

Imidazo[1,2-a]pyrazine 4b (500 mg, 4.20 mmol) was dissolved in 5 mL of 2-methoxyethanol, followed by addition of platinum dioxide (100 mg, 0.36 mmol), and the reactor was purged with hydrogen for three times. After stirring for 12 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to obtain 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 4c (200 mg, yield 38.7%) as a yellow oil. MS m/z (ESI): 124.1 [M+1]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Imidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Co., Ltd.; TANG, Pengcho; LI, Xin; LI, Xiangqin; CHEN, Yang; WANG, Bin; ZHU, Zhe; EP2604610; (2013); 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. 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of Imidazo[1,2-a]pyrazine-2-carboxylic acid

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

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:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2-Amirio-5-methylpyrazine (5.16 g, 47 itimol) was dissolved in CH2Cl2 (52 mL) , stirred and cooled to O0C under N2. To this, pyridine (4.8 mL, 59 ?unol) was added followed by phenyl chloroformate (6.2 mL, 59 mmol) , dropwise, over 15 min, causing a precipitate to form. The mixture was stirred at 0C for 1 h. Then the reaction was quenched with 0.25 M HCl (40 mL) and anhydrous ether (50 mL) , and stirred at O0C, for 30 min. The precipitate was isolated by filtration, washed with DI H2O (20 mL) and ether (2 x 25 mL) , and dried under vacuum to give the product (7.4 g) as a white fluffy powder .

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-Methylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ICOS CORPORATION; WO2006/105262; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 54608-52-5,Some common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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) 5-[5-(tert-Butoxycarbonylamino)-2-pyridyl]-1-(2-pyrazinyl)-1H-pyrazole-3-carboxylic acid ethyl ester 4-[5-(tert-Butoxycarbonylamino)-2-pyridyl]-2,4-dioxobutanoic acid ethyl ester (1.009 g) obtained in step 3) of Referential Example 20 and 2-hydrazinopyrazine (330 mg) obtained in Referential Example 2 were dissolved in ethanol (30 mL). The solution was refluxed for 88 hours, followed by cooling in air. The reaction solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol – chloroform). The product was further purified by silica gel thin-layer chromatography (methanol – chloroform), to thereby give 5-[5-(tert-butoxycarbonylamino)-2-pyridyl]-1-(2-pyrazinyl)-1H-pyrazole-3-carboxylic acid ethyl ester as an amorphous product (590 mg, 47%). 1H-NMR(400MHz,CDCl3)delta:1.43(3H,t,J=7.1Hz), 1.52(9H,s), 4.47(2H,q,J=7.1Hz), 6.55(1H,br s), 7.21(1H,s), 7.51(1H,d,J=8.5Hz), 8.01-8.08(1H,br m), 8.20(1H,dd,J=2.7,0.5Hz), 8.29(1H,dd,J=2.7,1.5Hz), 8.56(1H,d,J=2.7Hz), 9.02(1H,dd,J=1.5,0.5Hz). ESI-MS m/z:411(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 2-Hydrazinopyrazine, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1762568; (2007); 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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3BrN2

General procedure: 1,10-Phenanthroline (10.97 mg, 0.06 mmol) was added to 3-iodopyridine (94 mg, 0.46 mmol), 5 (p-TsOH salt, 100 mg, 0.30mmol), CuI (11.60 mg, 0.06 mmol), and K3PO4 (323 mg, 1.52mmol) in DMF (3 mL) at r.t. under nitrogen. The resultingmixture was stirred at 110 C for 1 d. The reaction mixture wasfiltered through a pad of Celite, and the filter cake was washedwith EtOAc (3 × 5 mL). The filtrate was concentrated to drynessunder reduced pressure to give a yellow residue which waspurified by flash silica chromatography, elution gradient 0-10%MeOH in CH2Cl2. Pure fractions were evaporated to dryness toafford 3a (49 mg, 68%) as an amorphous waxy yellow solid. Rf =0.41 (CH2Cl2-MeOH = 9:1). 1H NMR (400 MHz, CDCl3): delta = 8.56(1 H, d, J = 2.6 Hz), 8.48 (1 H, dd, J = 1.5, 4.8 Hz), 7.69 (1 H, ddd,J = 1.5, 2.6, 8.2 Hz), 7.32 (1 H, ddd, J = 0.7, 4.8, 8.2 Hz), 3.64 (2 H,s), 1.47 (7 H, s), 1.31 (6 H, s). N-H signal appeared under themethyl signal at delta = 1.47 ppm. 13C NMR (101 MHz, CDCl3): delta =174.4, 147.5, 146.8, 140.0, 133.3, 123.6, 62.5, 56.1, 49.7, 30.7 (2C), 27.9 (2 C). IR (): 3357, 3057, 2969, 2928, 1669, 1587, 1572,1467, 1434, 1402, 1347, 1302, 1283, 1246, 1206, 1173, 1151,1110 cm-1. HRMS (TOF ES+): m/z calcd for C13H19N3O [M + H]+:234.16009; found: 234.15987.

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alanine, Thomas A.; Stokes, Stephen; Scott, James S.; Synlett; vol. 28; 3; (2017); p. 357 – 361;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem