HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-Methoxy-4-{6-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl}phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol | HCID 2734650 | — |
| Reactant | 6-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amine | HCID 21919356 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-Methoxy-4-{6-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl}phenol | HCID 135474319 | 100.5% |
Reaction Steps
A mixture of 6-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amine (49 mg, 0.22 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (52 mg, 0.20 mmol), (PPh3)4Pd (23 mg, 0.020 mmol) and a Na2CO3 solution (0.22 mmol of a 2 M solution) in toluene (10 ml) was heated under reflux overnight. After removal of the solvents, the residue was dissolved in CH2Cl2 (150 ml), dried (Na2SO4), filtered and the CH2Cl2 removed in vacuo. The residue was purified by column chromatography, eluting with a n-hexane:ethyl acetate gradient mixture to obtain the desired product (62 mg, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07122550B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-731cb9b51f8341d28a8f9be59a95327f |
| Source note | uspto-grants-2006_10 |