HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile → 4-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile | HCID 2779072 | — |
| Reactant | 2-Iodopyrimidine | HCID 11356200 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile | HCID 19895589 | 64.8% |
Reaction Steps
0.63 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile, 0.75 g of 2-iodopyrimidine, 18 mg of triphenylphosphine, 12 mg of palladium(II) chloride and 3.5 mg of copper(I) iodide were stirred overnight in 20 ml of triethylamine under nitrogen. The mixture was evaporated to dryness and then ethyl acetate and water were added. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and subsequently ethyl acetate/petroleum ether (1:1) for the elution. There were obtained 580 mg of 4-[1,1-dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04971982 |
| Source dataset | uspto-grants-1990_11 |
| ORD ID | ord-567be858ccc245f8be7754c356f57004 |
| Source note | uspto-grants-1990_11 |