Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | HCID 86598204 | HCID 86598204 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69102413 | HCID 69102413 | 89.8% |
Reaction Steps
A mixture of 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide (200 mg), ethynylbenzen (331 mg), NEt3 (658 mg), triphenylphosphine (17 mg), CuI (6.2 mg), and PdCl2(PPh3)2 (23 mg) in DMF (2 ml) was heated at 80° C. for 18 hours. Water (20 ml) and EtOAc (20 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 (97:3). 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-(phenylethynyl)-2-pyrazinecarboxamide (218 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-41cbb52aa7974eb89d0af41ee3dda0ad |
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| Source note | uspto-grants-2008_08 |
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