Category: 6705-33-5

Synthetic Route of 6705-33-5, 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. 6705-33-5, name is Pyrazin-2-ylmethanol belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

1 eq. Preparation 2a, 2 eq. of pyrazin-2-ylmethanol and 2 eq. triphenylphosphine were dissolved in dry toluene (0.2M for the phenol), then 2 eq. DTAD was added. The mixture was stirred at 50 C under nitrogen atmosphere. After reaching an appropriate conversion the volatiles were removed under reduced pressure. The crude intermediate was purified via flash chromatography using heptane and EtOAc as eluents to obtain ethyl (2R)-2- acetoxy-3-[2-(pyrazin-2-ylmethoxy)phenyl]propanoate.

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

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; BALINT, Balazs; CSEKEI, Marton; SZABO, Zoltan; SZLAVIK, Zoltan; KOTSCHY, Andras; CHANRION, Maia; GENESTE, Olivier; CHEN, I-Jen; DAVIDSON, James Edward Paul; MURRAY, James Brooke; SIPOS, Szabolcs; ONDI, Levente; PROSZENYAK, Agnes; (164 pag.)WO2016/207217; (2016); 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. 6705-33-5, name is Pyrazin-2-ylmethanol belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C5H6N2O

Example 264; 4-[3,5-dimethyl-1-(pyrazin-2-ylmethyl)-1H-pyrazol-4-yl]benzonitrile A solution (0.090 mol/L, 2.2 mL) of 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzonitrile obtained in Reference Example 5 in THF was added to pyrazin-2-ylmethanol (37.1 mg) and the mixture was stirred. Cyanomethylene tri-N-butylphosphorane (about 250 mg) was added, and the mixture was stirred with heating at 60 C. for 31 hr. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexane, 0-30% methanol/ethyl acetate), and further by reversed-phase preparative HPLC (Gilson, UniPoint system, YMC ODS column 30×75 mm, 0.1% TFA containing acetonitrile-water (5:95-100:0)), and the eluted fraction was passed through ion-exchange resin, whereby the TFA salt was converted to a free form to give the title compound (23.1 mg).MS (ESI+, m/e) 290 (M+1)1H-NMR (DMSO-d6) delta: 2.16 (3H, s), 2.33 (3H, s), 5.47 (2H, s), 7.51 (2H, d), 7.87 (2H, d), 8.52 (1H, d), 5.89-8.63 (2H, m).

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); 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. 6705-33-5, name is Pyrazin-2-ylmethanol, This compound has unique chemical properties. The synthetic route is as follows., Safety of Pyrazin-2-ylmethanol

Step A: 3-chloro-4-(2-pyrazinemethoxyl)-nitrobenzene (compound 22.1).[0168] To a solution of 2-chloro-l-fluoro-4-mtro-benzene (875 mg, 5.0 mmol) in dryAcetone (10.0 ml) was added l.Og Of K2CO3 and 545mg of 2- pyrazinylmethanol(5.0mmol). The reaction mixture was then stirred at 650C overnight. Filtration and concentration gave a solid which was recrystallized to give the desired product as a red solid.

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 6705-33-5.

Reference:
Patent; KANIONUSA INC.; SHEN, Wang; ZHANG, Aimin; FAN, Junfa; ZHENG, Xiaoling; WO2011/2523; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6705-33-5, 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. 6705-33-5 name is Pyrazin-2-ylmethanol, 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.

Synthesis of 2-(chloromethyl)pyrazine [0540] To a stirred solution of pyrazin-2-ylmethanol (0.3 g 2.72 mmol) in DCM (10 mL) was added SOCl2 (1 mL) at 0 C under inert atmosphere. The reaction mixture was heated up to 50 C and stirred for 2 h. After completion of starting material (by TLC), the volatiles were evaporated under reduced pressure. The residue was quenched with ice cold water followed by saturated NaHC03 and extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford 2-(chloromethyl)pyrazine (110 mg, 20.4%) as liquid. 1H-NMR (CDC13, 400 MHz): delta 8.74 (s, 1H), 8.58-8.56 (m, 2H), 4.71 (s, 2H); LC-MS: 98.86%; 129 (M++l) (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 4.83 min. 5mM NH4OAc: ACN; 1.0 ml/min); TLC: 70% EtOAc/Hexane (Rf: 0.6).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazin-2-ylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6705-33-5,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.

To a solution of pyrazin-2-ylmethanol (55 mg, 0.5 mmol) in THF (4 mL) was added potassium tert-butoxide (110 mg, 1.0 mmol). After stirring for 10 min, Example 27G (100 mg, 0.25 mmol) was added to the reaction mixture in portions. The mixture was stirred at ambient temperature for 2 hours, quenched with saturated aqueous NH4Cl and extracted by EtOAc (3×10 mL). The combined organic extracts were concentrated under reduced pressure. Purification by flash chromatography (silica gel, MeOH/Et3N (10:1) in CH2Cl2 in 0-30% gradient) provided 61 mg (47%) of the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm 0.34-0.49 (m, 4H), 1.08-1.24 (m, 1H), 1.33-1.44 (m, 9H), 3.90 (s, 3H), 4.15 (d, J=7.1 Hz, 2H), 5.39 (s, 2H), 6.83 (s, 1H), 7.27 (d, J=8.8 Hz, 1H), 7.60 (dd, J=8.7, 1.9 Hz, 1H), 7.77 (d, J=2.4 Hz, 1H), 8.56-8.70 (m, 2H), 8.93 (d, J=1.4 Hz, 1H); MS (DCI/NH3) m/z 488 (M+H)+

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2010/69348; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Adding a certain compound to certain chemical reactions, such as: 6705-33-5, name is Pyrazin-2-ylmethanol, 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 6705-33-5, Safety of Pyrazin-2-ylmethanol

Pyrazin-2-ylmethanol (1.5 g) was dissolved in DMA (25 ml) and the solution was cooled to 0C. 60% Sodium hydride dispersion in oil (0.6 g) was added portionwise and the mixture was stirred for 10 minutes at 0C. A solution of 3-chloro-4-fluoronitrobenzene (2.18 g) in DMA (25 ML) was added over 15 minutes and the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. Saturated ammonium chloride (100 ml) was added, and the precipitated solid was filtered off and purified by chromatography eluting with 50% ethyl acetate/iso-hexane. The appropriate fractions were concentrated to give 3-chloro- 4- (2-PYRAZINYLMETHOXY) nitrobenzene as a brown solid (1.25 g, 38%).

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, Pyrazin-2-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26151; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6705-33-5, 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 6705-33-5 as follows.

Example 4; 4-Bromo-1-(2,2-dimethylpropyl)-5-(pyrazin-2-ylmethoxy)-1H-1,2,3-benzotriazole (Example 4-1) To a suspension of 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (Example 1-2) (1.5 g, 5.28 mmol, 1.0 equiv.), 2-pyrazinylmethanol (13) (0.581 g, 5.28 mmol, 1.0 equiv.) and polymer-supported triphenylphosphine (2.2 mmol/g, 5.75 g, 21.91 mmol, 2.5 equiv.) in THF (37.7 ml) and DCM (37.7 ml) was slowly added di-tert-butyl azodicarboxylate (2.431 g, 10.56 mmol, 2.0 equiv.). After stirring at room temperature for 1 hr, the reaction mixture was passed through a filter. The residue was washed with DCM and THF. The filtrate was concentrated to dryness to give a solid, which was taken up in DCM (12 mL) and treated with TFA (6 mL). The mixture was stirred at room temperature until LCMS showed only the desired product. The reaction mixture was neutralized to pH=7 with saturated aqueous NaHCO3, and then extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to obtain product Example 4-1. 1H NMR delta (CDCl3): 9.06 (s, 1H), 8.59-8.57 (m, 2H), 7.42 (d, 1H, J=9.5 Hz), 7.31 (d, 1H, J=9.0 Hz), 5.38 (s, 2H), 4.38 (s, 2H), 1.04 (s, 9H) ppm. LRMS m/z (M+H) 376.1 and 378.1 (intensity ratio 1:1) found, 376.1 and 378.1 required.

According to the analysis of related databases, 6705-33-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beshore, Douglas C.; Dudkin, Vadim; Garbaccio, Robert M.; Johnson, Adam W.; Kuduk, Scott D.; Skudlarek, Jason W.; Wang, Cheng; Fraley, Mark E.; US2012/135977; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6705-33-5, A common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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: These compounds were synthesized according to previously reported method.4 28a was purchased from commercial sources and used as received. To a solution of 27a-27c (1.0 mmol) in Et2O (10 mL) was added 60% NaH (1.0 mmol). The reaction mixture was stirred at rt for 10 min before adding trichloroacetonitrile (1.0 mmol) at once. The resulting solution was stirred for 2-5 h and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to yield the desired compounds 28a-28c.

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Yulong; Yang, Xicheng; Chen, Yiyi; Chen, Hao; Sun, Huijiao; Li, Wei; Xie, Qiong; Yu, Linqian; Shao, Liming; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2148 – 2152;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6705-33-5,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.

Dissolve 2-pyrazinylmethanol (2.0 g, 18.1 mmol) in DCM (200 mL) and cool to 0C while stirring under nitrogen. Add thionyl chloride (4.63 mL, 63.6 mmol) drop wiseover 10 mm, and allow to warm to 25 C. Stir at room temperature for 16 h. Concentrate the mixture and then dilute with DCM. Wash the crude solution with saturated NaHCO3, dry over Mg504, filter, and concentrate. Dissolve the crude residue in DCM and purify by silica gel flash chromatography (hexane/EtOAc, 95:5 to 100% EtOAc gradient) to give the title compound as a pale yellow oil. 1H NMR (400 MHz, CDC13) oe 4.67 (s = 2H),8.50-8.55 (m, 2H), 8.73 (s, 1H).

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

Reference:
Patent; ELI LILLY AND COMPANY; CHEDID, Marcio; EISSA, Hisham Omer; ENGLER, Thomas Albert; FURNESS, Kelly Wayne; RANK, Kenneth B.; WOODS, Timothy Andrew; WROBLESKI, Aaron D.; WO2015/69512; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem