Acetonitrile → HCID 135774058, compound

Temperature

150 °C

To each of 8 microwave tubes was added 2-amino-5-bromopyrazine (174 mg, 1.00 mmol), 2-hydroxyphenylboronic acid (151 mg, 1.10 mmol), acetonitrile (3 mL), dichlorobis(triphenylphosphine)palladium(II) (36 mg, 0.05 mmol), and a 1M aqueous sodium bicarbonate solution (1 mL). The 8 tubes were microwave-heated at 150° C. for 15 min. The reaction mixture was cooled and then poured into a solution of ethyl acetate and water. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in hot methanol (100 mL). The methanol solution was concentrated in vacuo until a precipitate was observed. The precipitate was filtered. The filtrate was further concentrated and filtered to afford 5-(2-hydroxy-phenyl)-pyrazin-2-ylamine (478 mg, 32%) as a solid.

1. temperatureThe reaction mixture was cooled
2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in hot methanol (100 mL)
7. concentrationThe methanol solution was concentrated in vacuo until a precipitate
8. filtrationThe precipitate was filtered
9. concentrationThe filtrate was further concentrated
10. filtrationfiltered

ORD record

ord-d334d13335e24f36880d68f596333e6f

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132425B2