HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenol → 5-Bromo-3-phenoxypyrazin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Amino-3,5-dibromopyrazine | HCID 620004 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Bromo-3-phenoxypyrazin-2-amine | HCID 17956021 | 64.6% |
Reaction Steps
Added sodium hydride (0.348 g, 8.70 mmol) to a solution of phenol (0.819 g, 8.70 mmol) in THF (50 mL) at 0° C. and stirred 30 minutes. Added 3,5-dibromopyrazin-2-amine (2.00 g, 7.91 mmol) in THF (10 mL). Removed the ice bath and refluxed overnight. Partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. Purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford the title compound (1.36 g, 64.6% yield) as a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883828B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-3e574ba7a29c4ba497c42a3d72ab1c9b |
| Source note | uspto-grants-2014_11 |