Category: 186534-02-1

Synthetic Route of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

5.5 g (36.7 mmol) of compound 1a-4The sample was dissolved in 30 ml of formic acid.Weigh 3.2g (45.9mmol)Hydroxylamine hydrochloride was added, followed by 3.13 g (45.9 mmol)Sodium formate, miscible, 120 C oil bath reaction reflux overnight.The pH of the reaction mixture was adjusted to 10 with a saturated aqueous sodium hydroxide solution and extracted with dichloromethane (30 ml*5 times). 100-200 mesh silica gel sample, dry sample column chromatography:Mobile phase EA: PE (1:5), TLC monitors the fraction of the effluent fraction,The compound 1a-5 fraction was collected. Combine the same fraction and distill dry,White solidCompound 1a-5, yield 65%.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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. HPLC of Formula: C8H10N2O

General procedure: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography. 3.2.1. 2,6-Bis-(3,5,6-trimethyl-pyrazin-2-ylmethylene)-cyclohexanone (5a)Yield: 74%; Mp: 112e113 C; 1H NMR (500 MHz, CDCl3) d: 7.87 (s,2H), 2.55 (s, 6H); 2.51 (s, 6H); 2.48 (s, 6H); 2.37 (t, J 8.0 Hz, 4H),1.85 (m, 2H); 13C NMR (500 MHz, CDCl3) d: 181.2,152.7,150.4,149.6,147.9, 146.2, 141.4, 27.9, 27.1, 17.1, 16.8, 16.1; HRMS (ESI) m/z:363.4754 [MH], Microanalysis calculated for C22H26N4O(362.47), C: 72.90%, H: 7.23%, N: 15.46%. Found C: 72.96%, H: 7.25%,N: 15.42%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 186534-02-1, its application will become more common.

Reference:
Article; Zha, Gao-Feng; Qin, Hua-Li; Youssif, Bahaa G.M.; Amjad, Muhammad Wahab; Raja, Maria Abdul Ghafoor; Abdelazeem, Ahmed H.; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 34 – 48;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 186534-02-1, A common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

10052] In 10 mL of methanol was dissolved 2,4-dimeth- ylphenylhydrazide hydrochloride (1.72 g, 10 mmol). To the solution, 3,5,6-trimethylpyrazine-2-carbaldehyde (1.50 g, 12 mmol) was added with an ice-bath under the protection of N2. After the mixture was stirred for 10 mm, a lot of brick red precipitate showed and the reaction was then complete. The mixture was filtered through a suction funnel, and the brick red solid was transferred to a vacuum oven to be dried for using directly in the next reaction step of the reaction. The red brick intermediate (3.04 g, 10 mmol) was dissolved in 25 mL of methanol, and 1.68 ml of anhydrous triethylamine and 1.7 ml of trifluoroacetic anhydride were added respectively with an ice-bath under the protection of N2, and the reaction was run for 30 minutes. The reaction was monitored by TLC till completion. The resulting material was extracted with Ethyl acetate, dried over anhydrous Na2504, separated by a silica gel colunm (ethyl acetate:petroleum ether=1 :3) to get T-006 as a light yellow solid (3.25 g, 89.3%). ESI-MS: [M+H] mlz 365.1. ?H-NMR (CDC13, 300 MHz) oe: 2.1 (s, 3H), 2.42 (s, 3H), 2.46 (s, 3H), 2.54 (s, 3H), 2.85 (s, 3H), 7.08 (d, j=7.05 Hz, 1H), 7.24 (d, J=7.21 Hz, 1H), 7.25 (s, 1H), 7.55 (s, 1H); Anal.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU MAGPIE PHARMACEUTICALS CO., LTD.; WANG, Yuqiang; CHEN, Haiyun; ZHANG, Zaijun; ZHANG, Gaoxiao; YU, Pei; SUN, Yewei; SHAN, Luchen; TAO, Liang; US2018/346430; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

10110] In a 50 mE round-bottom flask, freshly prepared TMP-CHO(lSOmg, 1 mmol)was addedanddissolvedin20 mE of 1 ,2-dichloroethane, propargylamine (66 mg, 1.2 mmol) was added slowly at room temperature, the reaction was run at room temperature for 2 hours, triacetoxy sodium borohydride (424 mg, 2 mmol) was added and monitored by TEC, about 2 hours later the reaction was complete, 10 mE of 10% K2C03 was added for quenching. The resulting material was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered and concentrated, and purified with silica gel colunm chromatography (ethyl acetate:petroleum ether 3:2) to give the compound MT-012 as a yellow solid (163 mg, 86%). ESI-MS: [M+H] mlz 190.3. ?H-NMR (CDC13): 3.96 (s, 2H); 3.56 (d, J=2.4 Hz, 2H); 2.51 (s, 3H); 2.49 (s, 6H); 2.26 (t, J=2.4 Hz, 1H).

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU MAGPIE PHARMACEUTICAL CO., LTD; WANG, Yuqiang; YOUDIM, Moussa B.H.; SUN, Yewei; ZHANG, Zaizun; ZHANG, Gaoxiao; YU, Pei; YI, Peng; LANG, Ming; LIU, Wei; (40 pag.)US2016/326099; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zha, Gao-Feng; Qin, Hua-Li; Youssif, Bahaa G.M.; Amjad, Muhammad Wahab; Raja, Maria Abdul Ghafoor; Abdelazeem, Ahmed H.; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 34 – 48;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

Example 1 Synthesis of TBN (FIG. 2) 2-[[(1,1-Dimethylethyl)oxidoimino]methyl]-3,5,6-trimethylpyrazine (TBN). To aldehyde 5 (1.9 g, 0.013 mol) in methanol (200 mL) was added tert-butylhydroxylamine (1 g, 0.011 mol), and the solution was refluxed for 2 h. Another portion of tert-butyl hydroxylamine (1 g, 0.011 mol) was then added, and the solution refluxed until aldehyde 5 was completely reacted. Solvent was removed in vacuo, and the product was extracted. The solution was dried with Na2SO4, and solvent removed in vacuo. The product was purified by column chromatography, eluding with ethyl acetate/petroleum ether (1/1, v/v), to produce TBN as a light yellow solid (1.1 g, 38% yield), mp: 68-70 C. 1H NMR (CDCl3, ppm): 7.82 (s, 1H), 2.47 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 1.63 (s, 9H). ESI-MS: 222 [M+H]+, 244 [M+Na]+. Anal. (C12H19N3O) C, H, N.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Yuqiang; Jiang, Jie; Yu, Pei; Sun, Yewei; Wang, Linda; Zhang, Zaijun; US2011/34485; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem