59489-71-3 | 2-Amino-5-bromopyrazine

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$9.00	$6.00
5g	98%	in stock	$11.00	$8.00
10g	≥98%	in stock	$15.00	$10.00
25g	≥98%	in stock	$23.00	$16.00
100g	98%	in stock	$57.00	$40.00
500g	98%	in stock	$281.00	$197.00

Description

• Catalog Number: AB61106
• Chemical Name: 2-Amino-5-bromopyrazine
• CAS Number: 59489-71-3
• Molecular Formula: C4H4BrN3
• Molecular Weight: 173.9987
• MDL Number: MFCD12761230
• SMILES: Nc1ncc(nc1)Br

Computed Properties

• Complexity: 77.7
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 8
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• XLogP3: 0.7

Upstream Synthesis Route

To synthesize 2-amino-5-bromopyrazine, one can start with pyrazinamide as the precursor. The first step involves bromination:

1. Pyrazinamide is treated with bromine in the presence of phosphorus tribromide (PBr3) or thionyl chloride (SOCl2), leading to simultaneous bromination at the C-5 position and conversion of the amide group to a bromine, yielding 5-bromopyrazine-2-carboxylic acid.

2. The carboxylic acid group of 5-bromopyrazine-2-carboxylic acid is reduced to an aldehyde using either lithium aluminum hydride (LiAlH4) or diborane (B2H6), followed by immediate oxidation with pyridinium chlorochromate (PCC) or manganese dioxide (MnO2), affording 5-bromopyrazine-2-carboxaldehyde.

3. The 5-bromopyrazine-2-carboxaldehyde is then converted to the corresponding hydrazone by reaction with hydrazine (N2H4), followed by oxidative cyclization using an oxidizing agent like hydrogen peroxide (H2O2) or ferric chloride (FeCl3). This step closes the pyrazine ring, yielding 2-amino-5-bromopyrazine.

It is important to note that each step may require careful control of reaction conditions and purification of intermediates to achieve the desired product with good yield and purity.

Literature

• Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines.

  The Journal of organic chemistry 20050107