Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | HCID 86598204 | HCID 86598204 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 69103551 | HCID 69103551 | 83.1% |
Reaction Steps
A mixture of 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide (500 mg), (4-methoxyphenyl)boronic acid (740 mg), and Pd(PPh3)4 (56.3 mg) in 2M aq. Na2CO3 (3.25 ml) and dioxane (20 ml) was refluxed for 3 hours. Water (40 ml) and of EtOAc (30 ml) were poured into the reaction mixture and the aqueous solution was extracted with EtOAc. The organic layer was washed with water and brine, and dried over MgSO4. After filtration, the solvent was removed under reduced pressure. The residual solid was placed on a column of silica-gel and eluted with CHCl3:MeOH (25:1). The eluent was evaporated and the residue was suspended with IPE and filtrated to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-(4-methoxyphenyl)-2-pyrazinecarboxamide (512 mg) as a yellow powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07407961B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-add6d6c627c547c2be5c47b3d71da311 |
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| Source note | uspto-grants-2008_08 |
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