HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (4-Benzyloxy-phenyl)-(6-(trimethylsilylethynyl)quinazolin-4-yl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | (4-Benzyloxyphenyl)-(6-iodoquinazolin-4-yl)-amine Hydrochloride | HCID 21951949 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (4-Benzyloxy-phenyl)-(6-(trimethylsilylethynyl)quinazolin-4-yl)-amine | HCID 22609859 | 81% |
Reaction Steps
The (4-benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine hydrochloride (1.0 g, 2.04 mmol) was reacted with trimethylsilylacetylene (8.0 ml, 5.56 g, 5.66 mmol), triethylamine (5.0 ml, 3.63 g, 3.58 mmol), bis(triphenylphosphine)palladium (II) chloride (0.10 g, 0.14 mmol) and copper(I)iodide (0.10 g, 0.53 mmol) at room temperature in acetonitrile (15 ml) under a nitrogen atmosphere overnight. Purification by silica gel chromatography (eluting with 50% i-hexane/EtOAc) gave the title compound as an off-white solid (0.70 g, 1.65 mmol, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06828320B2 |
| Source dataset | uspto-grants-2004_12 |
| ORD ID | ord-90651c7dbabc408294f8e27dca592215 |
| Source note | uspto-grants-2004_12 |