Category: 5521-58-4

Reference 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

Application of 5521-58-4,Some common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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 9: (/?)-l-[(5-Methyl-pyrazin-2-yIcarbamoyl)-methyl]-3-(l-thiophen-2-yl5 cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane bromide To a mixture of 5-methyl-pyrazin-2-ylamine and cesium carbonate (11.2 g) dissolved dry DMF (30 mL) was added by dropwise addition bromoacetylbromide (2.89 g) and mixture stirred at rt for 2 hours. Water (200 mL) was added and the mixture extracted ethyl acetate (2 x 100 mL) and dried over magnesium sulfate. Concentration of the exi to -50 mL and addition of ts°hexane (100 mL) gave the sub-titled compound as a sol (1-64 g).1H NMR (400 MHz, DMSO-D6) delta 1 1.06 (IH, s), 9.17 (IH, s), 8.31 (IH, d), 4.16 (2H, 2.46 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylpyrazin-2-amine, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); 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. Computed Properties of 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

Application of 5521-58-4, 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.

(a) 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 a white solid, m.p. 51-52 C.; mass spectrum (+ve CI): 188 (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; Zeneca Limited; US5866568; (1999); A;,
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. category: Pyrazines

l-Chloro-N,N.2-trimethyl-prop-l -en- 1 -amine (0.26 mL, 2.0 mmol) was added to a solution 5 of 3-[(2S)-l-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoic acid (0.54 g,1.5 mmol) in DCM (20 mL) and stirred for 1 hour. 5-Methylpyrazin-2-amine (ClambdaS no.5521-58-4) (335 mg, 3.1 mmol) then pyridine (0.25 mL, 3.1 mmol) were added and the reaction stirred for a further 30 minutes before being reduced in vacuo and partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was further extracted K) 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 residue was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the desired compound(0.48 g).1H NMR delta (CDCl3): 1.39 (d, 3H), 2.58 (s, 3H), 3.96 – 4.05 (m, 2H), 4.63 – 4.70 (m, IH), 15 5.13 (s, 2H), 6.30 (t, I H), 6.78 (t, IH), 7.09 (t, IH), 7.16 (t, IH), 7.35 – 7.48 (m, 5H), 8.17(s, IH), 8.39 (s, IH), 9.58 (d, IH); m/z 444 (M+H)+

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; WO2008/50117; (2008); 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. Product Details of 5521-58-4

Oxalyl chloride (0.17 mL, 1.94 mmol) and DMF (1 drop) were added to a solution of 3- {[(15)-l-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-l,4- benzoxazepin-8-yl)oxy]benzoic acid (625 mg, 1.56 mmol) in DCM (15 mL) and the mixture stirred at RT for 4 hours. The solvent was evaporated in vacuo to a residue which was added to a solution of 2-amino-5-methylpyrazine (255 mg, 2.34 mmol) and pyridine (0.64 mL, 7.8 mmol) in DCM (5 mL). The resultant mixture was heated at 6O0C in a microwave reactor for 5 minutes. The mixture was cooled to RT and pressure, the DCM was evaporated in vacuo to a residue which was partitioned between ethyl acetate (50 mL) and IN citric acid (25 mL). The organic layer was washed with IN citric acid (25 mL), brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (352 mg).1H NMR delta (CDCl3): 1.35 (d, 3H), 2.55 (s, 3H), 3.2 (s, 3H), 3.4 (s, 3H), 3.5 (m, 2H), 3.6 (t, 2H), 4.4 (t, 2H), 4.6 (m, IH), 6.6 (d, IH), 6.8 (dd, IH), 6.85 (m, IH), 7.15 (m, IH), 7.3 (s, IH), 7.9 (d, IH), 8.1 (s, IH), 8.45 (s, IH), 9.5 (s, IH); m/z 493 (M+H)+

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; WO2006/125972; (2006); 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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H7N3

A solution of HBr/CH3CO2H (360 g (260 mL), 1.50 mol, 33% HBr in CH3CO2H) in anhydrous CHCl3 (300 mL) was added over 15 min to a solution of 5-methylpyrazin-2-amine 15 (42 g, 0.38 mmol) in CHCl3 (1 L). The reaction flask was wrapped in aluminum foil and heated to 50 C for 30 min in the dark whereupon a solution of Br2 (68 g, 0.42 mmol) in CHCl3 (500 mL) was added dropwise over 3 h during which time the internal temperature of the reaction never exceeded 55 C. After 18 h at 55 C the solvent was evaporated under reduced pressure. The crude mixture was diluted with water (200 mL) and the pH was adjusted to pH=9 by the addition of solid Na2CO3. The suspension was filtered under vacuum and the filtrate was extracted with EtOAc (1 L×5). The combined organic extracts were concentrated under reduced pressure and purified by flash silica gel chromatography eluting with petroleum ether/EtOAc (5:1?1:1) to give compound 6-bromo-5-methylpyrazin-2-amine 17a (36 g, 50%) as a light orange solid; mp 154-157 C; IR (KBr): 3315, 3188, 1744, 1638, 1575, 1482, 1375, 1308, 1051 cm-1; 1H NMR (400 MHz, CDCl3): delta=7.84 (s, 1H), 4.55 (br s, 2H), 2.52 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=152.2, 141.8, 138.4, 129.2, 22.2; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9816 and 189.9796. An analytical sample of 3-bromo-5-methylpyrazin-2-amine (17b) was also isolated for spectroscopic analysis; mp 56-57 C. 1H NMR (400 MHz, CDCl3): delta=7.80 (s, 1H), 4.95 (br s, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=150.6, 142.8, 139.9, 125.2, 19.7; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9817 and 189.9796.

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

Reference:
Article; Harris, Anthony R.; Nason, Deane M.; Collantes, Elizabeth M.; Xu, Wenjian; Chi, Yushi; Wang, Zhihan; Zhang, Bingzhi; Zhang, Qingjian; Gray, David L.; Davoren, Jennifer E.; Tetrahedron; vol. 67; 47; (2011); p. 9063 – 9066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, 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.

Step 6: 5-Methoxy-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-2-trifluoromethyl-benzoic acid methyl ester. To a stirred solution of 5-methoxy-4-(4-nitro-phenoxycarbonylamino)-2-trifluoromethyl-benzoic acid methyl ester (878 mg, 2.1 mmol) in 4.2 mL NMP at room temperature under nitrogen was added 2-amino-5-methylpyrazine (232 mg, 2.1 mmol) and the reaction heated to 85 C. After six hours the reaction was cooled to room temperature and a precipitate formed. The precipitate was triturated with EtOAc (25 mL) and the urea isolated by filtration as a tan solid (470 mg, 58%).

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; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2-Amirio-5-methylpyrazine (5.16 g, 47 itimol) was dissolved in CH2Cl2 (52 mL) , stirred and cooled to O0C under N2. To this, pyridine (4.8 mL, 59 ?unol) was added followed by phenyl chloroformate (6.2 mL, 59 mmol) , dropwise, over 15 min, causing a precipitate to form. The mixture was stirred at 0C for 1 h. Then the reaction was quenched with 0.25 M HCl (40 mL) and anhydrous ether (50 mL) , and stirred at O0C, for 30 min. The precipitate was isolated by filtration, washed with DI H2O (20 mL) and ether (2 x 25 mL) , and dried under vacuum to give the product (7.4 g) as a white fluffy powder .

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, 5-Methylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ICOS CORPORATION; WO2006/105262; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

Examples (2R)-2-(3-Chloro-4-cyclopropanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid (Preparation 9) was coupled with amines selected from 2-amino-5-methylpyrazine, 3- amino-5-methylisoxazole, 3-aminoisoxazole, 2-amino-5-methylthiazole, 3-amino-6- methylpyridazine, l-methyl-3-aminopyrazole, 2-aminopyrazine and 4-aminopyrimidine using the following procedure to provide Examples 1-8.CH2Cl2 (6OmL) and DMF (0.08mL, 1.064mmol, 1.2 eq) were cooled to -100C and oxalylchloride slowly added (0.09mL, 0.465mol, 1.2 eq). After stirring for 15 min the reaction mixture was cooled to -300C and (2R)-2-(4-cyclopropanesulfonylphenyl)-3- (tetrahydropyran-4-yl)propionic acid (Preparation 8, 0.300g, 0.886mmol, 1.0 eq) was added.The reaction was stirred at -300C for 45min then pyridine (1.395mol, 0.3ImL in ImL CH2Cl2, 4.5eq) and the amine (4.43mmol, 5.0eq) were slowly added in parallel at -400C. The reaction mixture was stirred for 15min then the ice bath removed. The reaction mixture was stirred for 2h until it reached rt. The solvent was removed under partial vacuum and the crude mixture dissolved in EtOAc (1OmL) and aqueous HCl (1.5mL). The layers were separated and the aqueous phase extracted with EtOAc (5mL). The organic fractions were combined and washed with H2O (1OmL), saturated aqueous NaHCO3 (2 x 1OmL), water (5mL) and brine (5mL) and dried (MgSOzi). Purification was by flash chromatography (EtOAc :heptane, 2:1) and/or recrystallisation.

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; PROSIDION LTD; WO2007/51846; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem