Category: 5521-58-4

These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-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

DMAP (5%) was added to a solution of 5-methyl-pyrazin-2-ylamine (10 mmoles) in pyridine (50 ml) which was further treated with phenyl chloroformate (1.2 eq) and the reaction stirred at room temperature overnight. The mixture was added to 10Og of ice and the precipitate was filtered and washed with water and dried to give the title compound.

The synthetic route of 5-Methylpyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; WO2007/144579; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

(i) A solution of bromine (0.11 ml) in chloroform (20 ml) was added dropwise over 20 minutes to a solution of 2-amino-5-methylpyrazine (0.218 g) in chloroform (30 ml) which was protected from light. The reaction mixture was stirred for 90 minutes after addition was complete and was then washed with water (50 ml). The organic phase was dried (MgSO4) and volatile material was removed by evaporation to give a yellow oil. The oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-3-bromo-5-methylpyrazine (0.286 g) as white solid, m.p. 51-52 C.; mass spectrum (positive chemical ionisation (+ve CI)): 188 (M+H)+.

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; Zeneca Ltd.; US5668137; (1997); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4, These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-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.

[00790] To a mixture of 5-methylpyrazin-2-amine (10 g, 92 mmol) in DCM (300 mL) was added BS (16 g, 91.63 mmol) in one portion at 0 C under N2. The mixture was stirred at 30 C for 1 hr. The resulting mixture was poured into saturated aq. Na2S03 (100 mL) and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 3-bromo-5-methyl-pyrazin-2-amine (12 g, 69% yield,) as a light yellow solid. MR (400 MHz, CDCh-d) delta ppm 7.82 (s, 1H) 4.79 – 5.03 (m, 2 H) 2.39 (s, 3 H).

Statistics shows that 5-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 5521-58-4.

Reference:
Patent; REVOLUTION MEDICINES, INC.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; KOLTUN, Elena S.; AAY, Naing; BUCKL, Andreas; MELLEM, Kevin; SEMKO, Christopher; JOGALEKAR, Ash; KISS, Gert; GILL, Adrian; (298 pag.)WO2018/136265; (2018); 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5521-58-4

l-Chloro-N,N,2-trimethyl-l-propenylamine (0.1 mL, 0.75 mmol) was added to a solution of3-{[5-(azetidin-l-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[((15)-2-{[(l,l- dimethylethyl)(dimethyl)silyl]oxy}-l-meth.ylethyl)oxy]benzoic acid (0.3 g, 0.58 mmol) in DCM (10 mL) and stirred for 1 hour. 2-Amino-5-methylpyrazine (126 mg, 1.15 mmol) then pyridine (0.094 mL, 1.15 mmol) were added and the mixture stirred for a further 30 mins before being reduced in vacuo and partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was further extracted into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (MgSO4), and reduced in vacuo. The crude oil was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the title compound as an oil (180 mg). 1H NuMR delta (CDCl3): 0.00 (s, 3H), 0.03 (s, 3H), 0.82 (s, 9H), 1.28 (d, 3H), 2.35 (quin, 2H), 2.51 (s, 3H), 3.63 – 3.78 (m, 2H), 4.19 (t, 2H), 4.32 (t, 2H), 4.47 – 4.51 (m, IH), 6.95 (t, IH), 7.23 – 7.24 (m, IH), 7.35 (t, IH), 8.08 (s, IH), 8.12 (d, IH), 8.21 (d, IH), 8.45 (s, IH), 9.51 (d, IH); m/z 612 (M+H)+

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); 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 5521-58-4 as follows. Recommanded Product: 5521-58-4

l-Chloro-N,N,2-trimethyl-l-propenylamine (6.9 mL, 52.3 mmol) was added to a solution of 3-[(2S)-l-(difluoromethoxy)propan-2-ylJoxy-5-[5-(dimethylcarbamoyl)pyrazin-2- yl]oxy-benzoic acid (17.2 g, 41.8 mmol) in DCM (250 mL) and stirred at ambient temperature for 30 minutes. 5-Methylpyrazin-2-amine (9.1 g, 83.6 mmol) and pyridine (6.8 mL, 83.6 mmol) were added and the reaction stirred overnight. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), washed with water (2 x 100 mL), citric acid (IN, 100 mL), saturated sodium bicarbonate solution (2 x 100 mL) and saturated brine (10 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica, eluting with a gradient of 25-100% ethyl acetate in isohexane to afford the product as a colourless foam (11.2 g).

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/50117; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

l-Chloro-N,N,2-trimethyl-l-propenylamine (0.042 mL, 0.31 mmol) was added to a solution of 3- { [5-(azetidin- 1 -ylcarbonyl)pyrazin-2-yl]oxy }-5- { [(Ii?)- 1 -methyl-2- (methyloxy)ethyl]oxy}benzoic acid (0.102 g, 0.0.31 mmol) in DCM (3 mL) under argon and stirred at RT for 40 minutes. 2-Amino-5-methylpyrazine (57 mg, 0.52 mmol) and pyridine (0.043 mL, 0.52 mmol) were added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue taken up in ethyl acetate (30 mL), washed with water (2 x 10 mL), a saturated aqueous solution of sodium bicarbonate (10 mL), brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo. The crude material was chromatographed on silica, eluting with a gradient of 60-100% ethyl acetate in isohexane, to give the desired compound as a white foam (86 mg). SUP>1H NMR delta (CDCl3): 1.35 (d, 3H), 2.32 – 2.44 (m, 2H), 2.56 (s, 3H), 3.41 (s, 3H), 3.47 – 3.64 (m, 2H), 4.26 (t, 2H), 4.62 (q, IH), 4.69 (t, 2H), 6.98 (s, IH), 7.29 (s, IH), 7.41 (s, IH), 8.13 (s, IH), 8.35 (s, 2H), 8.86 (s, IH), 9.54 (s, IH); m/z 479 (M+H)⁺

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

3-{[5-(Azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(5-methylpyrazin-2-yl)benzamide To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]benzoic acid (1.0 eq), and acetonitrile (10 vols) followed by pyridine (3 eq) under a nitrogen atmosphere. Thionyl chloride (1.2 eq) as a solution in acetonitrile (0.225 vols) was added slowly, drop-wise via syringe pump over at least 2 hours. 5-Methylpyrazin-2-amine (1.2 eq) was added to the mixture as a solid. After 2.5 hours the reaction was quenched by adding toluene (10 vols) and 1.0M sodium carbonate solution (2.5 eq). The layers were separated. The organic layer was retained in the flask, then 1.0M hydrochloric acid (1.94 eq) was added. The mixture was agitated for 15 minutes then separated. The organic layer was washed with two aliquots of water (5 vols) then the solvent was removed on the rotary evaporator. Toluene (5 vols) was added to the residue, and warmed to 45 C. Isohexane (1.7 vols) was added, the mixture was seeded, and allowed to cool to ambient temperature overnight. The mixture was cooled to 0 C. for 4 hours, and then cooled to -10 C. for 3 hours. The solid was isolated by filtration then washed with isohexane (2.5 vols). After drying in the vacuum oven at 40 C. overnight, the desired product was obtained as a solid (corrected yield 85%).

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

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

5521-58-4, name is 5-Methylpyrazin-2-amine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C5H7N3

Palladium (II) acetate (lOmg) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene(40mg) were added to a mixture of S-4-chloro-6-methyl-2-{2-[3-(pyrid-2-yl)isoxazol-5- yl]pyrrolidin-l-yl}pyrimidine (272mg, 0.80mmol), 2-amino-5-methylpyrazine (85mg, 0.78mmol) and cesium carbonate in 1,4-dioxane (5ml) under nitrogen. The mixture was heated at 100C in a sealed vessel under microwave irradiation for 18 hours. The solution was allowed to cool, the insolubles were removed by filtration and the solvent was removed from the filtrate by evaporation. The residue was purified by column chromatography on silica gel eluting with EtOAc / hexane (25:75 increasing in polarity to 0:100). The purified product was triturated with ether and hexane and the solid collected by filtration to give the title compound (174mg, 53%); NMR (398K) 2.03-2.15 (2H, m), 2.15-2.20 (IH, m), 2.15 (3H, s), 2.35-2.45 (IH, m), 2.38 (3H, s), 3.70-3.75 (IH, m), 3.76-3.84 (IH, m), 5.45-5.55 (IH, m), 6.48 (IH, s), 6.65 (IH, s), 7.40-7.46 (IH, m), 7.85-7.90 (IH, m), 7.90-7.95 (IH, d), 8.10 (IH, s), 8.61-8.65 (IH, d), 9.10 (IH, s), 9.30-9.35 (IH, br s); m/z 415 [MH]+ .

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/31745; (2007); 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., 5521-58-4

[0386] A mixture of 5-methylpyrazine-2-carboxylic acid (2.76 g, 20 mmol) and oxalyl chloride (1.83 mL, 2.66 g, 21 mmol) in methylene chloride (40 mL) was treated with N,N-dimethylformamide (0.5 mL), and the mixture was stirred at 25 C. for 1 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give an oily solid. The solid was dissolved in acetone (120 mL) at 0 C. and then sodium azide (1.03g, 20 mmol) in water (50 mL) was added dropwise. After the addition was complete, stirring was continued at 0 C. for 30 min. The mixture was then poured into ice cold water (100 mL) and extracted with methylene chloride (3¡Á100 mL). The combined organic extracts were washed with water (1¡Á100 mL), a mixture of a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution (1:1, 1¡Á100 mL), and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated in vacuo to give 5-methyl-pyrazine-2-carbonyl azide (1.46 g, 45%) as a tan solid. The 5-methyl-pyrazine-2-carbonyl azide (500 mg, 3.07 mmol) was combined with benzyl alcohol (0.63 mL, 663 mg, 6.14 mmol) at 25 C. The mixture was then slowly heated on an oil bath to 90 C., upon which gas was violently evolved. The oil bath temperature was maintained until gas evolution ceased. The oil bath temperature was raised to 120 C. and stirring was continued for 10 min at that temperature. The mixture was cooled and triturated with diethyl ether/hexanes (1:4) to give (5-methylpyrazin-2-yl)-carbamic acid phenyl ester (438 mg, 58%) as a yellow solid. The (5-methylpyrazin-2-yl)-carbamic acid phenyl ester (500 mg, 2.2 mmol) and 10% palladium on carbon (212 mg) were mixed in ethanol (30 mL). The reaction vessel was flushed with hydrogen, and the mixture was stirred at 25 C. for 1 h under hydrogen (1 atm). The excess hydrogen was evacuated from the reaction vessel, and the mixture was filtered through a pad of celite. Concentration of the filtrate in vacuo gave 2-amino-5-methylpyrazine (183 mg, 76%) as a tan solid which was used without further purification. [0387] A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid (prepared as in Example 60, 263 mg, 0.73 mmol) and triphenylphosphine (250 mg, 0.95 mmol) in methylene chloride (5.0 mL) cooled to 0 C. was treated with N-bromosuccinimide (167 mg, 0.95 mmol) in small portions. After the complete addition of N-bromosuccinimide, the reaction mixture was allowed to warm to 25 C. over 30 min. The bright orange reaction mixture was then treated with 2-amino-5-methylpyrazine (160 mg, 1.46 mmol) and 2,6-lutidine (0.36 mL, 2.92 mmol). The resulting reaction mixture was stirred at 25 C. for 4 h. The reaction mixture was then diluted with methylene chloride (25 mL) and was successively washed with a 10% aqueous hydrochloric acid solution (1¡Á20 mL), a saturated aqueous sodium bicarbonate solution (1¡Á20 mL) and water (1¡Á20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 65/35 hexanes/ethyl acetate to 3/7 hexanes/ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-methyl-pyrazin-2-yl)-3-(4-oxo-cyclohexyl)-propionamide (158 mg, 48%) as a white foam: [alpha]23589=-41.52 (c=0.33, chloroform); EI-HRMS m/e calcd for C20H21Cl2N3O4S (M+H)+ 450.1249, found 450.1253.

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Reference:
Patent; Corbett, Wendy Lea; Grimsby, Joseph Samuel; Haynes, Nancy-Ellen; Kester, Robert Francis; Mahaney, Paige Erin; Racha, Jagdish Kumar; Sarabu, Ramakanth; Wang, Ka; US2003/225283; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5521-58-4, Name is 5-Methylpyrazin-2-amine, 5521-58-4, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

To a clean dry flask was added 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoic acid (1.0 mol eq), tetrabutylammonium chloride (0.01 eq), and toluene (10 L/kg). Thionyl chloride (1.5 eq) was added in one go and the reaction heated to 60 C. for 2 hours. The reaction mixture was distilled to an oil at 40 C. on the rotary evaporator, and acetonitrile (4 L/kg) added.To a second clean dry flask was added 5-methylpyrazine-2-amine (1.0 mol eq), pyridine (3.0 mol eq) and acetonitrile (4 L/kg). The acid chloride solution was added to the amine solution over 30 minutes at 22 C. and then allowed to agitate overnight.The reaction mixture was distilled to an oil at 40 C. on the rotary evaporator, and toluene (4 L/kg) added. The reaction mixture was distilled to give an oil at 40 C. on the rotary evaporator, then toluene (10 L/kg added) followed by water (4 L/kg) and 1.0M hydrochloric acid (4 L/kg). The reaction mixture was agitated at 22 C. for 30 minutes, whereupon it crystallized, and toluene (4 L/kg) and water (4 L/kg) was added.The reaction mixture was filtered and washed sequentially with water 2¡Á(2 L/kg), then toluene 2¡Á(2 L/kg).The filtrate was agitated overnight at 22 C. and further crystallisation was observed. The reaction mixture was filtered. The solids were dried to give the title compound as an off-white solid in 35% yield.1H NMR delta (400 MHz DMSO) 10.86 (bs, 1H), 9.75 (bs, 1H), 9.25-9.24 (s, 1H), 9.35 (s, 1H), 6.99 (t, 1H), 6.81 (t, 1H), 6.53-6.52 (t, 1H), 4.72-4.65 (m, 1H), 3.52-3.43 (m, 2H), 3.30 (s, 3H), 2.48 (s, 3H), 1.24-1.22 (d, 3H).

Statistics shows that 5-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 5521-58-4.

Reference:
Patent; AstraZeneca AB; US2010/210841; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem