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2-Amino-3-bromopyrazine

2-Amino-3-bromopyrazine structure

CAS No:
21943-12-4
Formula:
C4H4BrN3
Chemical Name:
2-Amino-3-bromopyrazine
Synonyms:
2-AMINO-3-BROMOPYRAZINE;3-bromopyrazin-2-amine;3-Bromo-pyrazinamine;3-BroMo-2-pyrazinaMine;Pyrazinamine, 3-bromo-
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Pharmaceutical Intermediates > Bulk Drug Intermediates

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2-Amino-3-bromopyrazine Basic Attributes

Molecular Weight：

174

Exact Mass：

172.958847

EC Number：

1312995-182-4

DSSTox ID：

DTXSID40563422

HScode：

2933990090

Characteristics

PSA：

51.8

XLogP3：

0.5

Density：

1.8±0.1 g/cm3

Boiling Point：

275.6°C at 760 mmHg

Flash Point：

120.5±25.9 °C

Refractive Index：

1.649

Vapor Pressure：

0.005mmHg at 25°C

2-Amino-3-bromopyrazine Use and Manufacturing

Compound C-01-A (0.6 g, 1.65 mmol) was dissolved in 10 mL of absolute ethanol, 2-amino-3-bromopyridine (0.575 g, 3.3 mmol) was added, Heated to reflux and reacted for 24 hours. To the reaction solution was added 20 mL of water, Filter, filter cake with 10mL water. Collect solid, Was added to a mixed solvent of 10 mL of isopropyl acetate and n-heptane (1: 2)Room temperature beating 3 hours. Filtered and dried at 40 C for 2 hours in vacuo, Gave C-01-B (0.55 g, 76%) as a light brown solid.A suspension of 2-amino-3-bromopyrazine (2.5 g, 19.3 mmol) in DME (20 mL) was added 3-bromo-1, 1, 1-trifluoroacetone (13.7g, 72.Ommol) and 4A molecular sieves (1.0 g). The reaction mixture was then stined at 90 C for 4h and quenched by the addition of water (25mL).This mixture was extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to give 8-chloro-2-trifluoromethyl-imidazo [1, 2-a] pyrazine (0.8g, 25%). 'H NMR (400 MHz, CDC13): oe 8.13- 8.10 (m, 2H), 7.84-7.82 (m, 1H); LC-MS: 268.3.0 [M+2Hj.General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the ortho-haloaminopyridine and BrettPhos G1 precatalyst (6 mol %). The vial was sealed with a teflon screw cap, and evacuated and backfilled with argon three times. The amine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were added with the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MS indicated complete conversion of the starting material. The mixture was cooled to room temperature, diluted with dichloromethane, and poured into water. The organic phase was separated and the aqueous phase was extracted twice more with dichloromethane. The combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure.

Computed Properties

Molecular Weight:174.00
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:172.95886
Monoisotopic Mass:172.95886
Topological Polar Surface Area:51.8
Heavy Atom Count:8
Complexity:77.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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