Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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 75907-74-3, name: (3,5,6-Trimethylpyrazin-2-yl)methanol

To a solution of (3,5,6-trimethylpyrazin-2-yl)methanol(4) (15.50 g, 102 mmol) in anhydrous CH2Cl2 (300 mL),thionyl chloride (7.41 mL, 102 mmol) was added drop bydrop at 0 C. After finishing dropping, the mixture wasstirred at room temperature for 2.5 h. The solvent was evaporatedin vacuo and the product 2-chloromethyl-3,5,6-trimethylpyrazine hydrochloride (5) was obtained as yellowsolid (21.11 g, 100%), mp: 102-105 C [11].

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:
Article; Li, Zhenyu; Yu, Fang; Cui, Lei; Chen, Wenmin; Wang, Shouxun; Zhan, Peng; Shen, Yuemao; Liu, Xinyong; Medicinal Chemistry; vol. 10; 1; (2014); p. 81 – 89;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63286-28-2, A common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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.

2-Chloro-3-hydrazinylpyrazine C-1 (15.6 g; 108 mmol) is slurried up in (300 ml) THF and cooled down in an ice bath to -5 C. Trifluoroacetic anhydride (17 ml; 118 mmol) is also dissolved in 300 ml THF and dropped slowly to the first solution. After 1 h most of the THF is evaporated, than a small amount of water is added and the mixture is extracted with DCM. The organic phase is dried over MgSO4 and evaporated to dryness. Yield: 100%. HPLC-MS: (M+H)+=241/243; tRet=1.31 min; method FSUN2.

The synthetic route of 63286-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; GIANNI, Davide; SMETHURST, Christian; US2014/142098; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

Svnthesis 2-1-A 6-Chloropyrazin-2-amine 2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous ammonia (28%, 10 mL) and heated to 100C overnight in a sealed tube. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave the title compound as a white solid (2.28 g, 17.6 mmol, 91%). 1H NMR (d6-DMSO, 400 MHz) delta 7.80 (d, 1 H1 J = 0.4 Hz), 7.70 (d, 1 H, J = 0.4 Hz), 6.9 (br s, 2H). LC-MS (2) rt 1.05 min; m/z (ESI+) 130/132.

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 875781-43-4, 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. 875781-43-4 name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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.

Step 1To a 500 ml three necked round bottom flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g,0.0252 mole) was taken in CH2C12 (150 ml). The reaction mixture was cooled to 0 C and diethylaluminiumchloride (1M solution in hexanes) (9.11 g, 0.0756 mole) was added drop wise at the same temperature under nitrogen atmosphere. The reaction mixture was stirred for 30 min at 0 C followed by slow addition of pivoloyl chloride (29.45 g, 0.2444 mole) over 15min at the same temperature. After completion of the addition, the reaction mixture was warmed up to RT Attorney Docket No. 11913-1008 and then up to 40 C and stirred for 16 hrs. The completion of the reaction was monitored on TLC using hexanes: ethyl acetate (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was poured in saturated NaHC03 solution with stirring at 10 C, diluted with CH2C12 and filtered through high flow. The filtrate was collected and washed with brine solution. Layers were separated and the aq. Layer was extracted with CH2C12. The combined organic layer was dried over Na2S04, filtered and concentrated to afford crude product which was subjected for the column purification. The crude compound was purified using column purification by eluting the compound with 10 -25% ethyl acetate in hexanes to yield 5.3g of l-(2- bromo-5H-pyrrolo[2,3-b] pyrazine-7-yl)- 2,2-dimethyl propan-l-one

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
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 369638-68-6 as follows. Recommanded Product: 369638-68-6

5-Methylpyrazin-2-amine To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added tert-butyl (5-methylpyrazin-2-yl)carbamate (1.0 eq), and water (6.85 vols). The mixture was heated to 70 C. and trifluoroacetic acid (TFA) (1.2 eq) was added slowly drop-wise over 90-120 minutes. Water (0.22 vols) was added to wash the TFA into the flask. The reaction mixture was heated at 65-75 C. for at least 30 minutes, and then cooled to 15-25 C. Then 32% w/w sodium hydroxide (1.30 eq) was added drop-wise over 30-60 minutes maintaining the reaction temperature between 15-40 C. Water (0.22 vols) was added to wash the sodium hydroxide into the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20 C. The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20 C. The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask. This process was repeated twice. The combined organic layers were filtered through a filter containing silica (20% w/w) into a clean dry flask. The mixture was heated to 40 C. and then vacuum distilled to a final volume of 1.0-1.33 vols. Toluene (3.0 vols) was added, and the vacuum distillation continued at 40 C. to a final volume of 1.0-1.33 vols. This process was repeated twice. The resulting mixture was cooled to 5 C., and agitated for 1 hour at this temperature then filtered, washed with toluene (0.3 vols) at 0-5 C. The batch is slurry washed with toluene (1.0 vol) at 0-5 C. After drying at 45 C. overnight, the desired product was obtained as a solid (corrected yield typically 75%). 1H NMR delta (400 MHz CDCl3): 7.92 (s, 1H), 7.87 (s, 1H), 4.6 (bs, 2H), 2.40 (s, 3H)

According to the analysis of related databases, 369638-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/210621; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXXX) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXXXI) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous NaaSO/t, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXXXII) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (265 pag.)WO2017/24010; (2017); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-6-chloropyrazine

A. 6-Methylpyrazine-2-ylamine. To a solution containing 6-chloro-2- pyrazineamine (5.0 g, 38.75 mmol) in 1,4-dioxane (70 mL) was added [1,3- bis(diphenylphosphino]Ni(II)Cl2 (2.10 g, 38.76 mmol), followed by drop-wise addition of dimethylzinc in toluene (38.75 mL, 2.0 M, 77.50 mmol), over 15 min. The solution was allowed stir at 105 °C for 16 hours. The solution was then condensed under reduced pressure, diluted with ethyl acetate and filtered through celite to remove the nickel salts. The resultant slurry was purified via Biotage silica gel chromatography (0-8percent methanol in dichloromethane) to afford the title compound as an orange solid (1.18 g, 28percent yield). MS (ESI) m/z 1 10.3 [M+ 1]+.

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; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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. name: 2,6-Dichloropyrazine

Preparation of compound 16a: 3,5-dichloro-2-methylpyrazineTo a solution of n-BuLi (78 mL, 0.195 mol) in dry THF (1.5 L) was added TMP (27.5 g, 0.195 mol) at -65 0C. After the addition, the mixture was warmed to 0 0C and stirred for 30 min at this temperature, the reaction mixture was then re-cooled to -78 0C and 2,6-dichloropyrazine (20 g, 0.13 mol) in THF (50 mL) was added into the mixture dropwise. The mixture was stirred for 30 min at -78 0C, then CH3I (65 g, 0.68 mol) was added and the reaction mixture was slowly warmed to rt and stirred for 3 h. The mixture was concentrated and diluted with H2O (300 ml_), extracted with DCM (4×100 ml_). The combined organic layer was washed with saturated NH4CI aqueous and water, dried over Na2SO4, concentrated and the residue was purified by chromatography which gave the title compound 16a (10 g, 47.6%).

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

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); 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. 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H6BrN3O

EXAMPLE 50 Sodium hydride (60% dispersion in oil; 0.198 g) was suspended in dimethoxyethane (5 ml) and 2-amino-5-bromo-3-methoxypyrazine (0.405 g) was added with stirring. After 15 minutes, 2-biphenylsulphonyl chloride (0.5 g) was added and the mixture was stirred for 18 hours. The reaction mixture was poured into water (20 ml) and acidified to pH2 with concentrated hydrochloric acid and extracted with ethyl acetate (3*25 ml). The combined organic extracts were evaporated and the residue was purified by flash chromatography on silica gel (30 g), eluding with hexane/ethyl acetate/glacial acetic acid (160/40/1 v/v), to give N-(5-bromo-3-methoxy-2-pyrazinyl)-2-biphenylsulphonamide (0.46 g); 1 H NMR (d6 -DMSO): 3.82(s,3H), 7.2-7.4(m,6H), 7.53-7.7(m,2H), 7.78(s,1H), 8.08(dd,1H), 10.33(br,1H); mass spectrum (+ve FAB, methanol/NBA): 420(M+H)+.

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 5900-13-0.

Reference:
Patent; Zeneca Limited; US5861401; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, 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 33332-29-5 as follows.

5-CHLORO-2-PYRAZINAMINE (D47, Step 1) (2.41 g, 18.6 MMOL) was dissolved in concentrated hydrochloric acid (24 ML), cooled in an ice-acetone bath and treated with a solution of sodium nitrite (2.63 g, 38.1 MMOL) in water (18 ML) dropwise over a period of 1 hour. The mixture was cooled in an ice-water bath and left to stir for 1 hour. The mixture was allowed to warm to room temperature over 1 hour, neutralised by addition of sodium hydroxide solution (2M) and extracted with dichloromethane. The DICHLOROMETHANE layers were combined, dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate: pentane (1: 9) to afford the title compound (0.33 g);’H NMR (CDCI3) 8.40 (2H, s).

According to the analysis of related databases, 33332-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem