HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Ethynylaniline → 6-[(4-aminophenyl)ethynyl]-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Ethynylaniline | HCID 3760025 | — |
| Reactant | 6-iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide | HCID 86615747 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 6-[(4-aminophenyl)ethynyl]-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine | HCID 67521091 | 65.9% |
Reaction Steps
6-Iodo-N4-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}pyrimidine-4,5-diamine hydroiodide (270 mg) was dissolved in a mixed solvent of acetonitrile (10.3 mL)/triethylamine (7.72 mL), and 4-ethynylaniline (80.3 mg), trans-dichlorobis(triphenylphosphine)palladium(II) (20.8 mg) and copper(I) iodide (7.16 mg) were sequentially added. The title compound (134 mg) was obtained as a powder by the reaction in the same manner as in Example 9 (iv).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07507740B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-2ab1f8bae8a043e4b9fa9fee77ad79a2 |
| Source note | uspto-grants-2009_03 |