Sodium Carbonate → HCID 18180219, Verbindung

A mixture of 2-amino-3-bromo-6-acetamidopyrazine (7.00 g, 0.03 mole) in benzene (60.90 ml) and tetrakis(triphenylphosphine)palladium(0) was stirred under nitrogen at room temperature for 10 minutes. 2M aqueous sodium carbonate (30.24 ml) was added to the mixture followed by a solution of 2,3,5-trichlorobenzene boronic acid (6.83 g, 0.03 mole) in absolute ethanol (7.07 ml) and the mixture refluxed under nitrogen for 17 hrs. A further equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was then added and the mixture refluxed for an additional 7.50 hrs. Finally, another equivalent of 2,3,5-trichlorobenzene boronic acid in absolute ethanol was added to the mixture and continued refluxing for 17 hrs. The cooled mixture was evaporated in vacuo. The residue was dissolved in chloroform (150 ml), washed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was purified by ‘flash chromatography’ using chloroform to 98:2 chloroform:methanol as the eluent. Yield 3.02 g (30%), M.p. 200-203° C.

1. temperaturethe mixture refluxed under nitrogen for 17 hrs
2. temperaturethe mixture refluxed for an additional 7.50 hrs
3. temperaturecontinued refluxing for 17 hrs
4. customThe cooled mixture was evaporated in vacuo
5. dissolutionThe residue was dissolved in chloroform (150 ml)
6. washwashed with aqueous saturated sodium bicarbonate (1×100 ml) and water (1×100 ml)
7. dry with materialdried over anhydrous magnesium sulphate
8. filtrationfiltered
9. customthe filtrate evaporated down in vacuo
10. customThe residue was purified by ‘flash chromatography’

ORD-Eintrag

ord-acd5a89d4873491a8ef4a6769496ed15

Quelldatensatz

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06599905B2