HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Pyridinamine, 5-iodo- | HCID 88579 | — |
| Reactant | Tetrahydro-2-(2-propynyloxy)-2H-pyran | HCID 98609 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 5-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamine | HCID 22397241 | 50% |
Reaction Steps
2-(2-Propynyloxy)tetrahydro-2H-pyran (360 mg), 5-iodo-2-pyridinylamine (440 mg), CuI (140 mg) and dichlorobis(triphenylphosphine)palladium (60 mg) are dissolved in diethylamine (10 mL). After the mixture is stirred for 1 h at room temperature, water (40 mL) and CH2Cl2 (80 mL) are added. The organic layer is separated, dried (MgSO4) and concentrated. The resulting residue is purified on a silica gel plate (CH2Cl2/methanol, 9/1) to give 230 mg (50%) of the title compound as an oil which slowly solidifies. MS (ESI+) m/z 233 (M+H)+. 1H NMR (CDCl3) δ 8.10, 7.60, 6.65, 5.90, 4.86, 4.48, 3.90, 3.5-3.6, 1.55-1.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06559145B2 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-dbf94253ffb1440d9bb7917fd401397f |
| Source note | uspto-grants-2003_05 |