59489-71-3

Basic information

• Product Name: 2-Amino-5-bromopyrazine
• Synonyms: 5-BROMOPYRAZINAMINE;5-BROMOPYRAZIN-2-AMINE;5-BROMO-PYRAZIN-2-YLAMINE;5-BROMO-2-PYRAZINAMINE;BUTTPARK 29\02-91;2-aimo-5-bromopyrazine;5-Bromo-2-aminopyrazine;2-AMINO-5-BROMOPYRAZINE: TECH.
• CAS NO: 59489-71-3
• Molecular Formula: C4H4BrN3
• Molecular Weight: 174
• EINECS: 1308068-626-2
• Product Categories: Amines and Anilines;Heterocycles;pharmacetical;Halides;Pyrazines, Pyrimidines & Pyridazines;Pyrazine;Nucleotides and Nucleosides;Pyrazines;Chloropyrazines, etc.;Bases & Related Reagents;Nucleotides;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrazinesHeterocyclic Building Blocks;Amines;Aromatics;Building Blocks/Intermediates;amine| alkyl bromide
• Mol File: 59489-71-3.mol
• Article Data: 47

Chemical Properties

• Melting Point: 113-117 °C(lit.)
• Boiling Point: 274.2 °C at 760 mmHg
• Flash Point: 119.7 °C
• Appearance: Brown Needles
• Density: 1.844 g/cm³
• Vapor Pressure: 0.00547mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Ethanol, Ethyl Acetate, Methanol
• PKA: 1.66±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-bromopyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromopyrazine(59489-71-3)
• EPA Substance Registry System: 2-Amino-5-bromopyrazine(59489-71-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/38-43-44-36/37/38-20/21/22
• Safety Statements: 26-37/39-45-36/37/39-22-36/
• WGK Germany: 3
• Hazardous Substances Data: 59489-71-3(Hazardous Substances Data)

Usage

Uses

Used without prior protection of the amino group in a palladium-catalyzed cross-coupling with pyridylboronic acids leading to pyrazinylpyridines.

InChI:InChI=1/C4H4BrN3/c5-3-1-8-4(6)2-7-3/h1-2H,(H2,6,8)

Synthetic route

2-amino-3,5-dibromopyrazine (24241-18-7) → 5-amino-2-bromopyrazine (59489-71-3)

Conditions	Yield
With trifuran-2-yl-phosphane; palladium diacetate; triethylamine Reagent/catalyst; Solvent; regioselective reaction;	97%

2-Aminopyrazine (5049-61-6) → 5-amino-2-bromopyrazine (59489-71-3)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent;	89%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃;	88%
With N-Bromosuccinimide In dichloromethane at 0℃; for 3.5h;	81.5%

2-Aminopyrazine (5049-61-6) → 5-amino-2-bromopyrazine (59489-71-3) + 2-amino-3,5-dibromopyrazine (24241-18-7)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 100℃; for 0.0833333h; Solvent; Temperature; Microwave irradiation;	A 88% B 6%
With N-Bromosuccinimide In dichloromethane at 0 - 5℃; for 2h;	A 62% B 12%
With N-Bromosuccinimide In dichloromethane at 0℃; for 2h;	A 62% B 12%
With pyridine; bromine In chloroform for 3h; Ambient temperature; 1.2 equivalent of bromine and pyridine;	A 36% B 10%

2-amino-3,5-dibromopyrazine (24241-18-7) → 2-Aminopyrazine (5049-61-6) + 5-amino-2-bromopyrazine (59489-71-3)

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In dimethyl sulfoxide regioselective reaction;	A 10% B 87%

2-Aminopyrazine (5049-61-6) → 5-amino-2-bromopyrazine (59489-71-3) + 3-bromo-pyrazine-2-amine (21943-12-4)

Conditions	Yield
With bromodioxane In 1,4-dioxane at 100℃; for 0.5h; Reagent/catalyst; Solvent;	A 48% B 6%

2-Aminopyrazine (5049-61-6) → 5-amino-2-bromopyrazine (59489-71-3) + 3-bromo-pyrazine-2-amine (21943-12-4) + 2-amino-3,5-dibromopyrazine (24241-18-7)

Conditions	Yield
With pyridine; bromine In chloroform for 3h; Ambient temperature; 1.1 equivalent bromine and pyridine;	A 35% B 0.5% C 7%

3-amino-6-bromo-pyrazine-2-carboxylic acid (486424-37-7) → 5-amino-2-bromopyrazine (59489-71-3)

Conditions	Yield
With tetralin

5-amino-2-bromopyrazine (59489-71-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-N’-(5-bromopyrazin-2-yl)-N,N-dimethylformamidine (1245215-89-7)

Conditions	Yield
at 60℃; for 2h;	100%
In isopropyl alcohol at 80℃; for 4h;	57%

5-amino-2-bromopyrazine (59489-71-3) + 3-methoxycyclobutane-1-carboxylic acid → N-(5-bromopyrazin-2-yl)-3-methoxycyclobutanecarboxamide

Conditions	Yield
Stage #1: 5-amino-2-bromopyrazine; 3-methoxycyclobutane-1-carboxylic acid With pyridine In acetonitrile at 20℃; for 0.0833333h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; acetonitrile at 20℃; for 12h;	100%

5-amino-2-bromopyrazine (59489-71-3) + Cyclobutanecarbonyl chloride (5006-22-4) → N-(5-bromopyrazin-2-yl)cyclobutanecarboxamide

Conditions	Yield
With pyridine at 0℃; for 0.25h;	100%

zinc(II) cyanide (557-21-1) + 5-amino-2-bromopyrazine (59489-71-3) → 2-amino-5-cyanopyrazine (113305-94-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 100℃; for 2h;	100%

5-amino-2-bromopyrazine (59489-71-3) + 4-methoxyphenylboronic acid (5720-07-0) → 2-amino-5-(4'-methoxyphenyl)-1,4-pyrazine (119738-50-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide Suzuki-Miyaura Coupling; Reflux;	99%
With bis(benzonitrile)palladium(II) dichloride; sodium carbonate; 1,4-di(diphenylphosphino)-butane In ethanol; toluene for 24h; Heating;	78%
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; methanol; water for 7h; Reflux;
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;

5-amino-2-bromopyrazine (59489-71-3) + acetyl chloride (75-36-5) → N-(5-bromopyrazin-2-yl)acetamide (174680-67-2)

Conditions	Yield
With pyridine In dichloromethane for 1h;	99%

5-amino-2-bromopyrazine (59489-71-3) + phenylboronic acid (98-80-6) → 2-amino-5-phenylpyrazine (13535-13-2)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; isopropyl alcohol at 150℃; for 0.166667h; microwave reactor;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene at 105℃; for 5h; Inert atmosphere;	92.8%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 12h; Suzuki Coupling; Inert atmosphere; Reflux; regioselective reaction;	74%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; N,N-dimethyl-formamide; toluene at 87℃; Reagent/catalyst; Solvent; Time; Inert atmosphere; Large scale;	1.82 kg
With bis(benzonitrile)palladium(II) dichloride; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; sodium carbonate In ethanol; water; toluene Reflux;

5-amino-2-bromopyrazine (59489-71-3) + diethylzinc (557-20-0) → 2-amino-5-ethylpyrazine (13535-07-4)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane; toluene at 12 - 21℃; for 4h; Inert atmosphere;	99%

5-amino-2-bromopyrazine (59489-71-3) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(5-bromopyrazin-2-yl)cyclopropanecarboxamide

Conditions	Yield
With pyridine at 0℃; for 15h;	99%

5-amino-2-bromopyrazine (59489-71-3) + pivaloyl chloride (3282-30-2) → N-(5-bromo-pyrazin-2-yl)-2,2-dimethylpropionamide (710322-28-4)

Conditions	Yield
With pyridine In ethanol; dichloromethane; water	98.21%
With pyridine In dichloromethane at 0 - 25℃; for 22.5h;	82%
With pyridine In dichloromethane at 0 - 25℃; for 22.5h;	82%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	82%

5-amino-2-bromopyrazine (59489-71-3) + acetic anhydride (108-24-7) → N-(5-bromopyrazin-2-yl)acetamide (174680-67-2)

Conditions	Yield
at 20℃; for 12h;	98%
Product distribution / selectivity;

5-amino-2-bromopyrazine (59489-71-3) + 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (126726-62-3) → 5-isopropenylpyrazin-2-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;	97%

5-amino-2-bromopyrazine (59489-71-3) + tert-butylisonitrile (119072-55-8, 7188-38-7) + benzaldehyde (100-52-7) → C16H17BrN4 (1021950-89-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;	96%

5-amino-2-bromopyrazine (59489-71-3) + tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-74-1) → tert-butyl 4-(4-(5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling; Inert atmosphere; Sealed tube;	96%

5-amino-2-bromopyrazine (59489-71-3) + 4-butylphenylboronic acid (145240-28-4) → C14H17N3

Conditions	Yield
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	96%

5-amino-2-bromopyrazine (59489-71-3) + (4-octylphenyl)boronic acid (133997-05-4) → C18H25N3 (1353879-67-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In water; acetonitrile for 6h; Suzuki-Miyaura coupling; Reflux;	95%

5-amino-2-bromopyrazine (59489-71-3) + 2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) + Benzyl isocyanide (88333-03-3, 10340-91-7) → N-benzyl-6-bromo-2-(2-bromo-4,5-dimethoxyphenyl)imidazo[1,2-a]pyrazin-3-amine (1402350-37-1)

Conditions	Yield
With perchloric acid In methanol at 20℃;	95%

5-amino-2-bromopyrazine (59489-71-3) + potassium cyanide (151-50-8) → 2-amino-5-cyanopyrazine (113305-94-5)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h; Heating / reflux;	94.4%
With copper(l) iodide; 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 2h; Heating;	88%
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In N,N-dimethyl-formamide at 200℃; for 1h;	36%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In N,N-dimethyl-formamide at 20℃; Heating / reflux;

potassium cyanide + 5-amino-2-bromopyrazine (59489-71-3) → 2-amino-5-cyanopyrazine (113305-94-5)

Conditions	Yield
With copper(l) iodide; 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h; Heating / reflux;	94.4%

5-amino-2-bromopyrazine (59489-71-3) + sodium cyanide (143-33-9) + copper(I) cyanide (544-92-3) → 2-amino-5-cyanopyrazine (113305-94-5)

Conditions	Yield
In N,N-dimethyl-formamide at 120℃;	93%
In N,N-dimethyl-formamide at 120℃;	93%
In N,N-dimethyl-formamide at 120℃;	93%

5-amino-2-bromopyrazine (59489-71-3) + 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (25016-12-0) → (5-bromo-pyrazin-2-yl)-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)amine (945978-42-7)

Conditions	Yield
In acetic acid	93%
In acetic acid	93%
With trimethylamine-borane; acetic acid In methanol at 20℃;	93%

5-amino-2-bromopyrazine (59489-71-3) + furan-3-boronic acid (55552-70-0) → 5-furan-3-yl-pyrazin-2-ylamine

Conditions	Yield
With sodium carbonate; tetrakis (triphenylphosphine) palladium (0) In 1,2-dimethoxyethane; ethanol; water for 0.75h; Heating / reflux;	92.5%

5-amino-2-bromopyrazine (59489-71-3) + cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexanecarboxylic acid (5-bromo-pyrazin-2-yl)-amide (940959-31-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1h;	92%

5-amino-2-bromopyrazine (59489-71-3) + Thiram (137-26-8) → 5-aminopyrazin-2-yl dimethylcarbamodithioate

Conditions	Yield
With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 110℃; for 48h; Sealed tube;	92%

5-amino-2-bromopyrazine (59489-71-3) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(5-aminopyrazin-2-yl)benzoate (1021918-64-8)

Conditions	Yield
Stage #1: 5-amino-2-bromopyrazine; 4-methoxycarbonylphenylboronic acid With potassium phosphate In 1,4-dioxane; water at 20℃; for 1h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 16h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	91%
Stage #1: 5-amino-2-bromopyrazine; 4-methoxycarbonylphenylboronic acid With potassium carbonate In 1,4-dioxane; water at 20℃; for 0.666667h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 4h; Suzuki Coupling; Reflux;	57%
With sodium carbonate; 1,1'-bis-(diphenylphosphino)ferrocene In 1,4-dioxane; water at 100℃; for 16h;	50%
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 20℃; for 16h; Suzuki Coupling; Inert atmosphere; Reflux;
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;

5-amino-2-bromopyrazine (59489-71-3) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → 2-amino-5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazine (1137476-16-4)

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 60℃;	91%

5-amino-2-bromopyrazine (59489-71-3) + (2-methyl-4-(N-methylsulfamoyl)phenyl)boronic acid (1152274-62-8) → 4-(5-aminopyrazin-2-yl)-N,3-dimethylbenzenesulfonamide (1612287-91-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane at 100℃; for 3h; Schlenk technique; Inert atmosphere;	91%

5-amino-2-bromopyrazine (59489-71-3) → 2-amino-3,5-dibromopyrazine (24241-18-7)

Conditions	Yield
With N-Bromosuccinimide In chloroform at 0 - 20℃; for 6.5h; Solvent;	91%
With N-Bromosuccinimide In dichloromethane

5-amino-2-bromopyrazine (59489-71-3) + (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7) → 5-(p-tert-butyldimethylsilyloxyphenyl)-2-amino-1,4-pyrazine (549503-20-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene for 17h; Inert atmosphere; Reflux;	90.2%
With sodium carbonate; PdCl2(PPh2(CH2)4PPh2) In toluene for 24h; Suzuki reaction; Heating;	72%
With sodium carbonate; 1,4-di(diphenylphosphino)-butane; palladium dichloride In ethanol; water; toluene for 15h; Suzuki coupling; Reflux; Inert atmosphere;
With sodium carbonate; dichlorobis(triphenylphosphine)palladium[II] In ethanol; water; toluene
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; toluene at 80 - 150℃; Suzuki Coupling;

Upstream product

• 486424-37-7 3-amino-6-bromo-pyrazine-2-carboxylic acid 
• 24241-18-7 2-amino-3,5-dibromopyrazine 
• 5049-61-6 2-Aminopyrazine 

Downstream Products

• 23229-26-7 2-5-dibromopyrazine 
• 89323-09-1 5-aminopyrazine-2-carboxamide 
• 40155-43-9 5-amino-2-pyrazinecarboxylic acid 
• 119738-50-0 2-amino-5-(4'-methoxyphenyl)-1,4-pyrazine 
• 549503-20-0 5-(p-tert-butyldimethylsilyloxyphenyl)-2-amino-1,4-pyrazine 
• 710323-06-1 2-amino-5-(2,2-dimethylvinyl)pyrazine 
• 113305-94-5 2-amino-5-cyanopyrazine 
• 945978-35-8 (5-bromo-pyrazin-2-yl)-(4'-methyl-biphenyl-2-ylmethyl)-amine 
• 625114-44-5 N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionamide 
• 625114-61-6 N-(5-bromo-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionamide 
• 710322-41-1 N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide 
• 710322-16-0 N-(5-bromo-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide 
• 710322-98-8 N-(5-bromo-pyrazin-2-yl)-3-cyclopentyl-2(R)-(4-methanesulfonyl-3-methyl-pheny)-propionamide 
• 1032825-43-6 5-[4-(methylsulfonyl)phenyl]-2-pyrazinamine 

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