Category: 3149-28-8

3149-28-8, Adding some certain compound to certain chemical reactions, such as: 3149-28-8, name is 2-Methoxypyrazine, 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 3149-28-8.

To a solution of 2-methoxypyrazine (5.0g, 45.4mmol), in 40ml of anhydrous THF was added tributyltin hydride (15.0mL, 54.9mmol) and the resulting solution stirred under nitrogen at 0C. Cyclohexylcarbonyl chloride (8.0mL, 59.8mmol) was added over 10min and stirring continued until reaction completion in 20min as determined by TLC (neutral alumina, EtOAc/hexanes (1/19, v/v)). A 1M solution of HCl in methanol (20.0mL) was then added to the reaction mixture that was stirred under nitrogen at 0C until reaction completion in 30min as determined by TLC (SiO2, EtOAc/hexanes (2/3, v/v). The reaction mixture was quenched with 50mL of water, extracted with ethyl acetate (3×50mL), washed with saturated sodium bicarbonate (10mL), and then dried over anhydrous Na2SO4. Purification by silica gel flash column chromatography (100% hexanes: to remove tin by-products, followed by methanol / dichloromethane 2-5%) afforded 4-cyclohexanecarbonyl-1,2-dihydro-2-pyrazinone 3 (8.9g, 94%) as a pale yellow solid (mp 160-163C dec).

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 3149-28-8.

Reference:
Article; Williams, Alfred L.; St. Hilaire, Valentine R.; Tetrahedron; vol. 73; 48; (2017); p. 6712 – 6717;,
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. 3149-28-8, name is 2-Methoxypyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O

CuSCN (100 mg, 0.82 mmol) was stirred in 500 muL neat 2-MeOPyz (5.18 mmol) under Ar for 3 d at ambient temp. A yellow solid was collected by filtration, washed with ethyl ether, and dried under vacuum (154 mg, 81%). IR (cm-1): 2123 (strong, sharp), 1587, 1529 (strong), 1471, 1438, 1398, 1311, 1284, 1195, 1145, 1060, 1014 (weak), 1004 (strong, sharp), 837, 759, 617. Anal. Calc. for C6H6Cu1N3O1S1: Cu, 27.42; C, 31.10; H, 2.61; N, 18.13. Found: Cu, 26.48; C, 31.12; H, 2.42; N, 17.95%. TGA calcd for CuSCN: 52.5%. Found: 53.9% (75-105 C).

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ayala, Gerardo; Tronic, Tristan A.; Pike, Robert D.; Polyhedron; vol. 115; (2016); p. 257 – 263;,
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. 3149-28-8, name is 2-Methoxypyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3149-28-8

1) Preparation of 2-Iodo-3-methoxypyrazine To 20 ml of an anhydrous THF solution of 1.3 g of diisopropylamine was added 4.8 ml (2.5 M hexane solution) of n-butyllithium at -78 C., and the mixture was stirred at that temperature for 20 minutes. To the reaction mixture was added 10 ml of a THF solution of 1.1 of 2-methoxypyrazine, followed by stirring at -78 C. for 1 hour. To the reaction mixture was further added 10 ml of a THF solution of 4.0 g of iodine, followed by stirring for 4 hours while gradually elevating the temperature to room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform as a developing solution. The fraction containing the desired compound was concentrated to give 0.49 g of the title compound. 1H-NMR (CDCl3) delta: 4.02 (s, 3H), 7.94 (d, 1H, J=2.5 Hz), 7.99 (d, 1H, J=2.5 Hz).

According to the analysis of related databases, 3149-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US6169086; (2001); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 3149-28-8,Some common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, 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.

Representative procedure for the preparation of 1-phenoxycarbonyl-2-phenyl-3-methoxy-1,2-dihydropyrazine (3a). To a stirred solution of 2-methoxypyrazine (0.200 g, 1.816 mmol) inanhydrous THF (5 mL) was added phenylchloroformate (0.28 mL, 2.225 mmol) at 0 C andstirring was continued under nitrogen atmosphere until salt formation was completed (15 min, asdetermined by TLC on neutral alumina, EtOAc/hexanes 1:19). The reaction mixture was cooledto -41 C, a 1 M solution of phenylmagnesium bromide in THF (2.4 mL, 2.4 mmol) was addedand the mixture stirred until reaction completion (40 min, as determined by TLC on neutral SiO2,EtOAc/hexanes 1:9), and then quenched with 2 mL of aqueous 20% NH4OH/NH4Cl 1:1 (w/w).The mixture was extracted with dichloromethane (2 × 15 mL), dried over Na2SO4, andconcentrated in vacuo. Purification of the crude mixture by flash silica gel columnchromatography (0-15% EtOAc/hexanes) afforded 3a (0.488 g, 87%) as a white solid (3:2mixture of rotamers): mp: 81-82 C; 1H NMR (CDCl3, 500 MHz) delta 7.49-7.27 (m, 7H), 7.20 (t, J= 7.5 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.99 (d, J = 7.5 Hz, 1H), 6.67 and 6.63 (2d due torotamers, J = 5.5 Hz, 1H), 6.16 and 6.14 (2d due to rotamers, J = 5.0 Hz, 1H), 5.89 and 5.87 (2sdue to rotamers, 1H), 3.84 and 3.83 (2s due to rotamers, 3H); 13C NMR (CDCl3, 125 MHz) delta160.2, 160.0, 151.6, 151.5, 150.7, 150.4, 136.8, 135.9, 129.3, 128.8, 128.7, 128.6, 127.2, 126.6,125.9, 125.8, 121.3, 118.2, 118.1, 112.5, 111.8, 56.0, 54.6, 54.0, 53.9; HRMS (ESI) m/z calcdfor C18H17N2O3 [M + H]+ 309.12337, found 309.123554

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; St Hilaire, Valentine R.; Hopkins, William E.; Miller, Yenteeo S.; Dandepally, Srinivasa R.; Williams, Alfred L.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 72 – 78;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 3149-28-8, A common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, 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: Perfluorobutanesulfonyl azides 1a (715 mg, 2.2 mmol) and pyrazine 2a (2.0 mmol) was mixed without solvent at room temperature, this reaction mixture stirred for 8 h at 120 C, TLC analysis showed the reaction was completed. The product 3aa was obtained by flash column chromatography (using petroleum ether/ethyl acetate=2:1 as eluant) as a yellow solid in 34% yield (234 mg).

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xiong, Wanting; Zhang, Hongfei; Xin, Yong; Zhu, Shizheng; Tetrahedron; vol. 67; 12; (2011); p. 2232 – 2237;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 3149-28-8, 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 3149-28-8 as follows.

Alternate synthesis of (8) A solution of 5.4 ml of 2,2,6,6-tetramethylpiperidine, in 300 ml of dry THF was cooled to -8C as 19 ml of 1.6 M butyllithium (0.03 mol) in hexane was added dropwise. The reaction was stirred 20 min then cooled to -77C. A solution of 2.5 g of 2-methoxypyrazine (0.023 mol) in 5 ml of THF was added dropwise to the reaction. After 5h, 2.9 g of 3-quinuclidinone (0.023 mol) in 5 ml of THF was added dropwise and the reaction stirred another h. A solution of 8 ml of concentrated HCl and 4 ml of ethanol was added, the cooling was removed, and when the temperature reached -10C, 20 ml of 5 N NaOH was added. The volatile organics were evaporated and the residue extracted 3X with 50 ml of CHCl3 The extracts were washed with brine, dried, and the solvent evaporated to give a clear yellow liquid that solidified on further drying. Recrystallization from ether gave 3.53 g of (8) identical to the material produced in the previous reaction.

According to the analysis of related databases, 3149-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVO NORDISK A/S; EP521067; (1995); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 3149-28-8, A common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, 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.

To a solution of lithium 2,2,6,6-tetra-methylpiperidide (2.6 mmol, 0.5 M in THF) at -78 C was added a solution of 2-methoxypyrazine (220 mg, 2.0 mmol) in THF (5 mL). The reaction mixture was stirred at -78 C for 30 min. Ethyl formate (167 mg, 0.18 mL, 2.3 mmol) was added and stirring was continued for 30 min at -78 C. A mixture of hydrochloric acid (35% aq, 1 mL), ethanol (1 mL) and THF (4 mL) was added and the resulting mixture was warmed to room temperature, neutralized with NaHCO3 (satd, 5 mL) and evaporated to near dryness. The residue was extracted with dichloromethane (3×25 mL). The organic extract is dried (MgSO4) and reduced in vacuo. The crude residue was purified by flash column chromatography using n-hexanes/ethyl acetate (3:1) as eluent to give the title compound as a yellow solid (193 mg, 1.4 mmol, 70%); mp 47-49 C (lit.10 mp 66-67 C); numax (neat)/cm-1 2955, 2797, 1710, 1534, 1468, 1365, 1305, 1072, 954, 762; deltaH (400 MHz, CDCl3) 10.27 (1H, s, CHO), 8.37 (1H, d, J 2.4, CH), 8.35 (1H, d, J 2.4, CH), 4.13 (3H, s, Me); deltaC (100 MHz, CDCl3) 190.1 (CHO), 160.5 (C), 145.7 (CH), 137.5 (CH), 136.3 (C), 54.5 (Me); m/z (ESI) 161 (100%, [M+Na]+); HRMS (ESI, [M+Na]+) found 161.0322. [C6H6N2NaO2]+ requires 161.0321.

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Christy; Sperry, Jonathan; Tetrahedron; vol. 70; 21; (2014); p. 3430 – 3439;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, 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. Quality Control of 2-Methoxypyrazine

Preparation 37; 2-Methoxy-3- (3-methoxy-4-nitrophenyl) pyrazine (P37); 2,2, 6, 6-Tetramethylpiperidine (0.71 mL, 4.21 mmol) was added to a solution of n- butyllithium (1.6M, 2.6 mL, 4.16 mmol) in tetrahydrofuran (10 mL) at-30C. The mixture was allowed to warm up to 0C and stirred at that temperature for 15 minutes. The solution was then cooled to-70C, a solution of 2-methoxypyrazine (200 mg, 1.80 mmol) in tetrahydrofuran (5 mL) was added and then the mixture stirred at that temperature for 30 minutes. A solution of zinc chloride (500 mg, 3.67 mmol) in tetrahydrofuran (5 mL) was subsequently added at-70C and the mixture was then allowed to warm slowly to room temperature. A solution containing tetrakis (triphenylphosphine) palladium (0) (83 mg, 0.07 mmol) and 4-bromo-2-methoxy-1-nitrobenzene (459 mg, 1.98 mmol) in tetrahydrofuran (5 mL) was added to the organozinc derivative and the mixture heated at 65C for 2 hours. The reaction mixture was then hydrolyse with a solution containing ethylenediaminetetraacetic acid (1.1 g, 3.7 mmol) in water (10 mL) which had been made slightly basic with a saturated aqueous solution of potassium carbonate. The aqueous phase was extracted with dichloromethane (3×100 mL) and the combined extracts dried over magnesium sulfate and concentrated in vacuo. The product was purified by silica gel chromatography eluting with 0 to 80% ethyl acetate in hexane to yield the title compound as a solid ; MS (APCI+ve) : [M+H] + at m/z 262 (C12H11N304 requires [M+H] + at m/z 262).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3149-28-8, its application will become more common.

Electric Literature of 3149-28-8, A common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, 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.

1) Preparation of 2-Iodo-3-methoxypyrazine To 20 ml of an anhydrous THF solution of 1.3 g of diisopropylamine was added 4.8 ml (2.5 M hexane solution) of n-butyllithium at -78 C., and the mixture was stirred at that temperature for 20 minutes. To the reaction mixture was added 10 ml of a THF solution of 1.1 of 2-methoxypyrazine, followed by stirring at -78 C. for 1 hour. To the reaction mixture was further added 10 ml of a THF solution of 4.0 g of iodine, followed by stirring for 4 hours while gradually elevating the temperature to room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform as a developing solution. The fraction containing the desired compound was concentrated to give 0.49 g of the title compound. 1H-NMR (CDCl3) delta: 4.02 (s, 3H), 7.94 (d, 1H, J=2.5 Hz), 7.99 (d, 1H, J=2.5 Hz).

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US6169086; (2001); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 3149-28-8, The chemical industry reduces the impact on the environment during synthesis 3149-28-8, name is 2-Methoxypyrazine, I believe this compound will play a more active role in future production and life.

General procedure: Perfluorobutanesulfonyl azides 1a (715 mg, 2.2 mmol) and pyrazine 2a (2.0 mmol) was mixed without solvent at room temperature, this reaction mixture stirred for 8 h at 120 C, TLC analysis showed the reaction was completed. The product 3aa was obtained by flash column chromatography (using petroleum ether/ethyl acetate=2:1 as eluant) as a yellow solid in 34% yield (234 mg).

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-Methoxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiong, Wanting; Zhang, Hongfei; Xin, Yong; Zhu, Shizheng; Tetrahedron; vol. 67; 12; (2011); p. 2232 – 2237;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem