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Aminopyrazine, specifically 2-aminopyrazine, is an organic compound with the molecular formula C4H5N3. It is a heterocyclic compound featuring a pyrazine ring with an amine group attached to the second carbon. Aminopyrazine is known for its role as a synthetic intermediate in various chemical and pharmaceutical applications due to its reactive nature and ability to form diverse chemical structures.

5049-61-6

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5049-61-6 Usage

Uses

Used in Pharmaceutical Synthesis:
Aminopyrazine is used as a synthetic intermediate for the production of pharmaceutical compounds. It plays a crucial role in the synthesis of favipiravir, an antiviral medication used to treat influenza. Additionally, it is utilized in the four-component synthesis of imidazolidines, which are important building blocks for various pharmaceuticals and have applications in the development of new drugs.
Used in Synthetic Chemistry:
In the field of synthetic chemistry, Aminopyrazine serves as a versatile intermediate. It is involved in the formation of complex organic molecules through various chemical reactions. One such reaction involves the combination of 2-aminopyrazine with α-ketohydroximoyl chlorides to produce 3-nitrosoimidazo[1,2-a]pyrazines, which are valuable compounds in the synthesis of various organic compounds and pharmaceuticals.
Used in Chemical Research:
Aminopyrazine is also used in chemical research to study the properties and reactivity of heterocyclic compounds. Its ability to form various chemical structures makes it an interesting subject for researchers looking to understand the behavior of different functional groups and their potential applications in the development of new materials and compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 5049-61-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,4 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 5049-61:
(6*5)+(5*0)+(4*4)+(3*9)+(2*6)+(1*1)=86
86 % 10 = 6
So 5049-61-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H5N3/c5-4-3-6-1-2-7-4/h1-3H,(H2,5,7)

5049-61-6 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (A0989)  2-Aminopyrazine  >98.0%(GC)(T)

  • 5049-61-6

  • 5g

  • 290.00CNY

  • Detail
  • TCI America

  • (A0989)  2-Aminopyrazine  >98.0%(GC)(T)

  • 5049-61-6

  • 25g

  • 890.00CNY

  • Detail
  • Alfa Aesar

  • (A13052)  2-Aminopyrazine, 99%   

  • 5049-61-6

  • 5g

  • 489.0CNY

  • Detail
  • Alfa Aesar

  • (A13052)  2-Aminopyrazine, 99%   

  • 5049-61-6

  • 25g

  • 1790.0CNY

  • Detail
  • Alfa Aesar

  • (A13052)  2-Aminopyrazine, 99%   

  • 5049-61-6

  • 50g

  • 3380.0CNY

  • Detail
  • Aldrich

  • (A76958)  Aminopyrazine  98%

  • 5049-61-6

  • A76958-10G

  • 544.05CNY

  • Detail
  • Aldrich

  • (A76958)  Aminopyrazine  98%

  • 5049-61-6

  • A76958-50G

  • 1,882.53CNY

  • Detail
  • Fluka

  • (89132)  Aminopyrazine  matrix substance for MALDI-MS, ≥99.0% (NT)

  • 5049-61-6

  • 89132-10X10MG-F

  • 2,032.29CNY

  • Detail
  • Fluka

  • (89132)  Aminopyrazine  matrix substance for MALDI-MS, ≥99.0% (NT)

  • 5049-61-6

  • 89132-1G-F

  • 5,624.19CNY

  • Detail

5049-61-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Aminopyrazine

1.2 Other means of identification

Product number -
Other names Pyrazin-2-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5049-61-6 SDS

5049-61-6Synthetic route

2-iodopyrazine
32111-21-0

2-iodopyrazine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With copper(I) oxide; ammonia; potassium carbonate In 1,4-dioxane at 140℃; under 7757.43 Torr; for 16h;92%
With copper(I) oxide; ammonium hydroxide; potassium carbonate at 140℃; for 16h; Inert atmosphere;49%
2-amino-3,5-dibromopyrazine
24241-18-7

2-amino-3,5-dibromopyrazine

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

5-amino-2-bromopyrazine
59489-71-3

5-amino-2-bromopyrazine

Conditions
ConditionsYield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In dimethyl sulfoxide regioselective reaction;A 10%
B 87%
2-pyrazine carbonitrile
19847-12-2

2-pyrazine carbonitrile

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide at 20 - 60℃; for 5h;82.6%
With sodium hypochlorite; potassium hydroxide; sodium hydroxide at 40℃; for 2h; pH=8; Temperature;
With sodium hypochlorite; water; sodium hydroxide at -5 - 100℃;74 g
2-chloropyrazin
14508-49-7

2-chloropyrazin

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

di(pyrazin-2-yl)amine
533930-18-6

di(pyrazin-2-yl)amine

Conditions
ConditionsYield
With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Schlenk technique;A 79%
B n/a
2-chloropyrazin
14508-49-7

2-chloropyrazin

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;75%
With ammonia; water at 200℃;
With ammonia In dimethyl sulfoxide at 130℃;
phthalimide
136918-14-4

phthalimide

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

2-(5-Amino-pyrazin-2-ylmethyl)-isoindole-1,3-dione
457099-33-1

2-(5-Amino-pyrazin-2-ylmethyl)-isoindole-1,3-dione

Conditions
ConditionsYield
With sodium carbonate In CH2Cl2/MeOH; dichloromethane; trifluoroacetic acidA n/a
B 73%
1,4-pyrazine
290-37-9

1,4-pyrazine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With potassium permanganate; potassium amide In ammonia for 0.166667h;65%
2-fluoropyrazine
4949-13-7

2-fluoropyrazine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction;52%
2-(1-hydroxyethyl)pyrazine
94777-52-3

2-(1-hydroxyethyl)pyrazine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 12h;45%
N-cyclohexyl-2-phenylimidazo[1,2-a]pyrazin-3-amine

N-cyclohexyl-2-phenylimidazo[1,2-a]pyrazin-3-amine

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

N-cicloesil-α-ossofenilacetamide
724-92-5

N-cicloesil-α-ossofenilacetamide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;A n/a
B 28%
N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
475641-51-1

N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

1,4,8a,9-tetraaza-fluorene

1,4,8a,9-tetraaza-fluorene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; potassium carbonate In acetonitrile; benzene at 80℃; for 24h;A 20%
B 24%
N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
475641-51-1

N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide

benzene
71-43-2

benzene

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

1,4,8a,9-tetraaza-fluorene

1,4,8a,9-tetraaza-fluorene

C

3-phenyl-pyrido[1',2':2,3]pyrazolo[5,4-b]pyrazine

3-phenyl-pyrido[1',2':2,3]pyrazolo[5,4-b]pyrazine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; potassium carbonate In acetonitrile at 80℃; for 24h;A 20%
B 24%
C 20%
pyrazinamide
98-96-4

pyrazinamide

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sodium hypochlorite Behandeln des erhaltenen Natrium-Salzes der Pyrazinylcarbamidsaeure C5H5N3O2(Kristalle;Verfaerbung ab 257grad)mit wss.Saeuren.;
3-aminopyrazinoic acid
5424-01-1

3-aminopyrazinoic acid

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With diethylene glycol monoethyl ether acetate at 210 - 245℃;
With nitrobenzene
Erhitzen ueber den Schmelzpunkt;
Lumazine
487-21-8

Lumazine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sulfuric acid at 240 - 245℃;
Pyrazin-N-Oxid(PyzNO)
2423-65-6

Pyrazin-N-Oxid(PyzNO)

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sodium hydroxide; trichlorophosphate 1) 70 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
N-(Tetrazolyl-5')-2-pyrazinylamine
88002-29-3

N-(Tetrazolyl-5')-2-pyrazinylamine

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

[1,2,4] triazolo[1,5-a]pyrazin-2-amine
88002-33-9

[1,2,4] triazolo[1,5-a]pyrazin-2-amine

Conditions
ConditionsYield
With PPA at 290℃;
9-tert-butylfluorene
17114-78-2

9-tert-butylfluorene

C4H4N3(1-)*K(1+)

C4H4N3(1-)*K(1+)

A

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

B

potassium salt of 9-tert-butylfluorene
106358-48-9

potassium salt of 9-tert-butylfluorene

Conditions
ConditionsYield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With polystyrene Wang resin; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid 1.) toluene, 100 deg C, 16 h, 2.) CH2Cl2, 5 min; Yield given; Multistep reaction;
Lumazine
487-21-8

Lumazine

sulfuric acid
7664-93-9

sulfuric acid

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
at 240 - 245℃;
3-amino-pyrazine-carboxylic acid-(2)

3-amino-pyrazine-carboxylic acid-(2)

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
beim Erhitzen ueber den Schmelzpunkt;
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2-chloroethanal
107-20-0

2-chloroethanal

imidazo[1,2-a]pyrazine
274-79-3

imidazo[1,2-a]pyrazine

Conditions
ConditionsYield
at 70℃;100%
With sodium hydrogencarbonate at 100℃; for 48h; Inert atmosphere;50%
With sodium hydrogencarbonate at 100℃; for 48h;50%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

2-phenylimidazo<1,2-a>pyrazin-3(7H)-one
27955-58-4

2-phenylimidazo<1,2-a>pyrazin-3(7H)-one

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 168h;100%
With hydrogenchloride In ethanol at 20 - 25℃; for 18h;49%
With hydrogenchloride In ethanol; water at 20℃; for 15h; Cyclization;20%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

4-chlorophenylglyoxal
4998-15-6

4-chlorophenylglyoxal

2-(4-Chloro-phenyl)-7H-imidazo[1,2-a]pyrazin-3-one
123488-69-7

2-(4-Chloro-phenyl)-7H-imidazo[1,2-a]pyrazin-3-one

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 264h;100%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E)-N,N-dimethyl-N'-(pyrazin-2-yl)formimidamide

(E)-N,N-dimethyl-N'-(pyrazin-2-yl)formimidamide

Conditions
ConditionsYield
In toluene for 2.25h; Heating / reflux;100%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate
203866-18-6

methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate

(2S,4R)-1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide
1109790-67-1

(2S,4R)-1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 2-Aminopyrazine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃;
Stage #2: methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate In tetrahydrofuran at 20℃; for 4h;
100%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

water
7732-18-5

water

cadmium(II) acetate
543-90-8

cadmium(II) acetate

Cd(aminopyrazine)(acetate)2(H20)

Cd(aminopyrazine)(acetate)2(H20)

Conditions
ConditionsYield
In ethanol at 25℃;100%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2-aminopyrazine 1-oxide
21720-40-1

2-aminopyrazine 1-oxide

Conditions
ConditionsYield
With hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid In methanol; N,N-dimethyl-formamide at 25℃; for 1h;99%
With 3-chloro-benzenecarboperoxoic acid In acetone for 24h; Ambient temperature;63%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

benzaldehyde
100-52-7

benzaldehyde

N-cyclohexyl-2-phenylimidazo[1,2-a]pyrazin-3-amine

N-cyclohexyl-2-phenylimidazo[1,2-a]pyrazin-3-amine

Conditions
ConditionsYield
With lanthanum chloride heptahydrate In neat (no solvent) at 60℃; for 0.416667h; Green chemistry;99%
In neat (no solvent) at 20℃; for 2.5h; Sealed tube; Irradiation; Green chemistry;96%
In neat (no solvent) at 160℃; for 1.5h; Green chemistry;95%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

N-(2-nitrophenyl)pyrazin-2-amine

N-(2-nitrophenyl)pyrazin-2-amine

Conditions
ConditionsYield
With sodium phenoxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 80℃; for 2h;99%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2
912540-27-3

Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2

[Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2(aminopyrazine)]2
912540-09-1

[Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2(aminopyrazine)]2

Conditions
ConditionsYield
In tetrahydrofuran stirred soln. of Cu-complex and ligand in THF brought to boiling, cooled; Et2O slow diffused; elem. anal.;99%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

1-Naphthalenesulfonyl chloride
85-46-1

1-Naphthalenesulfonyl chloride

N-pyrazin-2-yl-1-naphthalenesulfonamide

N-pyrazin-2-yl-1-naphthalenesulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;99%
3-Chloropyridine
626-60-8

3-Chloropyridine

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

N-(pyridin-3-yl)-pyrazin-2-amine
1028223-88-2

N-(pyridin-3-yl)-pyrazin-2-amine

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(π-crotyl)Pd(BrettPhos)]OTf; potassium carbonate In tert-Amyl alcohol at 110℃; for 2h; Schlenk technique; Inert atmosphere;99%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(π-crotyl)Pd(BrettPhos)]OTf; potassium carbonate In tert-Amyl alcohol at 110℃; for 2h; Schlenk technique; Inert atmosphere;99%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2-amino-3,5-dibromopyrazine
24241-18-7

2-amino-3,5-dibromopyrazine

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 100℃; for 0.0833333h; Solvent; Microwave irradiation;98%
With 2,6-dimethylpyridine; bromine In dichloromethane95%
With bromine; sodium hydrogencarbonate In acetic acid 1.) 2h, 2.) 1h;91%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

N-o-tolylpyrazin-2-amine

N-o-tolylpyrazin-2-amine

Conditions
ConditionsYield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 20h;98%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 100℃; for 24h;74%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-[p-methylphenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
1094443-81-8

1-[p-methylphenyl(2-pyrazinylamino)methyl]naphthalene-2-ol

Conditions
ConditionsYield
In water at 20℃; for 0.666667h;98%
at 125℃; for 0.0666667h; Mannich reaction; Neat (no solvent);89%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

β-naphthol
135-19-3

β-naphthol

1-[p-chlorophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
1094443-78-3

1-[p-chlorophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol

Conditions
ConditionsYield
In water at 20℃; for 0.666667h;98%
at 125℃; for 0.0666667h; Mannich reaction; Neat (no solvent);90%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-[p-bromophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
1094443-85-2

1-[p-bromophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol

Conditions
ConditionsYield
In water at 20℃; for 0.416667h;98%
at 125℃; for 0.1h; Mannich reaction; Neat (no solvent);93%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2C21H11O6(3-)*C4H4N2*3Cu(2+)*H2O*13C3H7NO

2C21H11O6(3-)*C4H4N2*3Cu(2+)*H2O*13C3H7NO

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2C21H11O6(3-)*C4H5N3*3Cu(2+)*H2O*12C3H7NO

2C21H11O6(3-)*C4H5N3*3Cu(2+)*H2O*12C3H7NO

Conditions
ConditionsYield
at 120℃; for 6h; Autoclave;98%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

2,2,2-trifluoro-N-(pyrazin-2-yl)acetamide
129476-64-8

2,2,2-trifluoro-N-(pyrazin-2-yl)acetamide

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 48h; Reflux;97.8%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

triphenylphosphine
603-35-0

triphenylphosphine

1,1,1-triphenyl-N-(pyrazin-2-yl)-λ5-phosphanimine
69982-02-1

1,1,1-triphenyl-N-(pyrazin-2-yl)-λ5-phosphanimine

Conditions
ConditionsYield
With diethylazodicarboxylate In dichloromethane; toluene at 20℃; for 2.16667h; Mitsunobu type reaction;97%
With hexachloroethane; triethylamine In acetonitrile 12 h, RT, then, reflux, 6 h;64%
With hexachloroethane; triethylamine In benzene for 3h; Heating;64%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

2,3-dibromopyridine
13534-89-9

2,3-dibromopyridine

A

pyrido[3',2':4,5]imidazo[1,2-a]pyrazine

pyrido[3',2':4,5]imidazo[1,2-a]pyrazine

B

pyrido[2',3':4,5]imidazo[1,2-a]pyrazine

pyrido[2',3':4,5]imidazo[1,2-a]pyrazine

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 140℃; for 24h;A n/a
B 97%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

benzaldehyde
100-52-7

benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-[phenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
1094443-75-0

1-[phenyl(2-pyrazinylamino)methyl]naphthalene-2-ol

Conditions
ConditionsYield
In water at 20℃; for 0.583333h;97%
at 125℃; for 0.05h; Mannich reaction; Neat (no solvent);94%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

(pyrrolyl-1)-2 pyrazine
50966-75-1

(pyrrolyl-1)-2 pyrazine

Conditions
ConditionsYield
In water at 150℃; for 0.5h; Paal-Knorr condensation; Microwave irradiation;97%
5-Methylfurfural
620-02-0

5-Methylfurfural

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

N-cyclohexyl-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyrazin-3-amine
879592-50-4

N-cyclohexyl-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyrazin-3-amine

Conditions
ConditionsYield
Stage #1: 5-Methylfurfural; 2-Aminopyrazine With scandium tris(trifluoromethanesulfonate) In methanol at 20℃; for 1h; Ugi reaction;
Stage #2: Cyclohexyl isocyanide In methanol Ugi reaction;
97%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

methanol
67-56-1

methanol

N-methylpyrazin-2-amine
32111-28-7

N-methylpyrazin-2-amine

Conditions
ConditionsYield
With C19H37IrN4(2+)*2I(1-); potassium carbonate at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;97%
With [Cp*Ir(2-(1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazole)Cl][Cl]; caesium carbonate at 120℃; for 12h; Schlenk technique;95%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;90%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

1-(pyrazin-2-yl)pyrrolidin-2-ol

1-(pyrazin-2-yl)pyrrolidin-2-ol

Conditions
ConditionsYield
With cerium(III) chloride heptahydrate In acetonitrile at 60℃;97%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

2-ethynylbenzaldehyde
38846-64-9

2-ethynylbenzaldehyde

N-(tert-butyl)-2-(2-ethynylphenyl)imidazo[1,2-a]pyrazin-3-amine

N-(tert-butyl)-2-(2-ethynylphenyl)imidazo[1,2-a]pyrazin-3-amine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 12h; Inert atmosphere;96%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

tetraethyl [(pyrazin-2-ylamino)methylene]bis(phosphonate)
586344-70-9

tetraethyl [(pyrazin-2-ylamino)methylene]bis(phosphonate)

Conditions
ConditionsYield
With copper(II) oxide In neat (no solvent) at 60℃; Microwave irradiation; Green chemistry;96%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

diphenyl sulfide
139-66-2

diphenyl sulfide

N-phenylpyrazin-2-ylamine
13134-34-4

N-phenylpyrazin-2-ylamine

Conditions
ConditionsYield
With SingaCycle-A1; potassium hexamethylsilazane In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;96%
2-Aminopyrazine
5049-61-6

2-Aminopyrazine

water
7732-18-5

water

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

Zn(2+)*2C4H5N3*2C2H3O2(1-)*4H2O

Zn(2+)*2C4H5N3*2C2H3O2(1-)*4H2O

Conditions
ConditionsYield
at 25℃; for 2h;96%

5049-61-6Relevant articles and documents

Green Synthesis and Antimicrobial Activity of Some Novel N-Arylimidazo[1,2-a]pyrazine-2-Carboxamide Derivatives

Jyothi, Boggavarapu,Madhavi, Nannapaneni

, p. 84 - 90 (2020)

The article deals with the synthesis of some novel N-arylimidazo[1,2-a]pyrazine-2-carboxamides (7a-l) by condensation reaction of imidazo[1,2-a]pyrazine-2-carboxylic acid (5) with different aliphatic/aromatic amines (6a-l) by using 1-methylimidazole, Mukaiyama’s reagent and 2-chloro-1-methylpyridinium iodide under microwave irradiation conditions. A new series of compounds 7 have been prepared from 2-iodopyrazine (1). Compound 1 on purged with ammonia gas in the presence of Cu2O and K2CO3 furnishes pyrazin-2-amine (2), which is treated with ethyl 3-bromo-2-oxopropanoate (3) to produce ethyl imidazo[1,2-a]pyrazine-2-carboxylate (4), which on hydrolysis with NaOH yields imidazo[1,2-a]pyrazine-2-carboxylic acid (5). The structures of the newly synthesized compounds have been elucidated on the basis of spectral (IR, 1H and 13C NMR and MS) and analytical data. Compounds 7a-l have also been screened for their antimicrobial activity. Some of the compounds exhibit promising antimicrobial activity.

C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Ham, Won Seok,Choi, Hoonchul,Zhang, Jianbo,Kim, Dongwook,Chang, Sukbok

supporting information, p. 2885 - 2892 (2022/02/23)

Synthesis of heteroaryl amines has been an important topic in organic chemistry because of their importance in small-molecule discovery. In particular, 2-Aminopyrimidines represent a highly privileged structural motif that is prevalent in bioactive molecules, but a general strategy to introduce the pyrimidine C2-N bonds via direct functionalization is elusive. Here we describe a synthetic platform for site-selective C-H functionalization that affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products in situ. Mechanism-based reagent design allowed for the C2-selective amination of pyrimidines, opening the new scope of site-selective heteroaryl C-H functionalization. Our method is compatible with a broad range of pyrimidines with sensitive functional groups and can access complex aminopyrimidines with high selectivity.

Novel method for synthesizing 2- amino -3,5- dibromopyrazine as well as product and application thereof

-

Paragraph 0042; 0060-0061; 0066; 0071; 0077; 0078, (2020/03/25)

The invention discloses a novel method 2 - for synthesizing, amino - 333355-dibromopyrazine by reacting, with,aminopyrazine 2 - sodium hypochlorite as a raw material, and adding, amino-pyrazino,dibromopyrazine 2 - in ;amino - 3333,5-dibromopyrazine as a raw material by, hours N,N - to obtain,aminopypyrazine 1,3 - in step, as a solvent 2 - and dropping under reduced pressure. N,N - The present invention provides a novel method for synthesizing, amino-3,5-dibromopyrazine as a crude product 15 - 20 in a reduced pressure distillation condition . The present invention. discloses a process 2 - for the preparation of the product. 2 - The present invention discloses 2 - N - 3333,5-dibromopyrazino, crude, obtained by the present, invention is added dropwise to prepare 2 - lamino - 3333.5-dibromopyrazine.

Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex

-

Paragraph 0025; 0026; 0109, (2019/02/08)

The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.

Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides

Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian

, p. 8411 - 8422 (2019/05/17)

An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.

Copper-catalyzed arene amination in pure aqueous ammonia

Takagi, Mio,Watanabe, Ayako,Murata, Shigeo,Takita, Ryo

supporting information, p. 1791 - 1795 (2019/02/20)

A simple protocol for copper-catalyzed arene amination using aqueous ammonia without any additional ligands and organic coordinating solvents has been developed. The reaction pathway via a Cu(i)/Cu(iii) mechanism is proposed based on the results of control experiments as well as DFT calculations.

Aromatic amine compound synthesis method

-

Paragraph 0251-0253, (2019/01/23)

The invention discloses an aromatic amine compound synthesis method which is characterized in that the method is implemented according to any of two methods. The first method includes the steps: mixing an alkyl aromatic compound with a general formula (I) and a nitrogen-containing compound with a general formula (II); performing reaction on mixture under an oxidizing agent and an organic solvent to obtain an aromatic amine compound with a general formula (III). The second method includes the steps: mixing an aromatic alcohol derivative with a general formula (I') and the nitrogen-containing compound with the general formula (II); performing reaction on mixture under an acid additive and an organic solvent to prepare the aromatic amine compound with the general formula (III). According to the method, a lot of alkyl aromatic compounds or aromatic alcohol derivatives firstly serve as raw materials, and the raw materials are reacted to generate the aromatic amine compound without the action of metal catalysis. Compared with a traditional synthesis method, the synthesis method has the advantages that the method is high in yield and simple in condition, waste discharging amount is less,metal participation is omitted, a reaction device is simple, industrial production is easily achieved and the like. The method has a wide application prospect.

Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride

Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu

supporting information, p. 7564 - 7567 (2018/11/02)

Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.

A 2 - amino pyrazine derivatives of preparation method

-

Paragraph 0012; 0013; 0014, (2018/10/19)

The invention discloses a 2 - amino pyrazine derivatives of preparation method, comprises the following steps: C1: to 2 - cyano pyrazine is sequentially added in the sodium hypochlorite solution and alkali, then stirring, to obtain 2 - amino pyrazine; C2: step C1 of the obtained 2 - amino pyrazine join the brominating agent performing the bromination reaction, to obtain 2 - amino - 3, 5 - two bromine pyrrole qin; C3: step C2 of the obtained 2 - amino - 3, 5 - two bromine pyrrole qin with morpholine substitution reaction to obtain 2 - amino - 5 - bromo - 3 - morpholinyl pyrazine solution; C4: the 2 - amino - 5 - bromo - 3 - morpholinyl [...] is distilled out of the organic solvent, then wash the static separation, to obtain 2 - amino - 5 - bromo - 3 - morpholinyl pyrazine crude product. In order to 2 - cyano pyrazine as raw materials, is easy to prepare or procurement, after acid-base reaction, bromination reaction, the substitution reaction, distillation filtering and the like four-step operation preparation, preparation method is simple and convenient operation, the final preparation of the obtained 2 - amino pyrazine derivatives have high yield, is suitable for industrial production.

Selective Cross-Coupling of (Hetero)aryl Halides with Ammonia to Produce Primary Arylamines using Pd-NHC Complexes

Lombardi, Christopher,Day, Jonathan,Chandrasoma, Nalin,Mitchell, David,Rodriguez, Michael J.,Farmer, Jennifer L.,Organ, Michael G.

supporting information, p. 251 - 254 (2017/04/26)

Herein we report the first example of (hetero)arylation of ammonia using a monoligated palladium-NHC complex. The new, rationally designed, precatalyst (DiMeIHeptCl)Pd(allyl)Cl featuring highly branched alkyl chains has been shown to be effective in selective aminations across a range of challenging substrates, including nitrogen-containing heterocycles and those featuring base-sensitive functionality. The less bulky Pd-PEPPSI-IPentCl precatalyst performs well for ortho-substituted aryl halides, giving monoarylated products in high yield with good selectivity.

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