HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylamine → 6-(Pyrimidin-5-YL)hex-5-YN-1-OL
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | 5-Hexyn-1-ol | HCID 70234 | — |
| Reactant | 5-Bromopyrimidine | HCID 78344 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 6-(Pyrimidin-5-YL)hex-5-YN-1-OL | HCID 13999752 | 86.5% |
Reaction Steps
A mixture of 5-bromopyrimidine (3.96 g), 5-hexynol (2.44 g), dicyclohexylamine (4 g) and acetonitrile (50 ml) was de-oxygenated by bubbline nitrogen through the solution for 10 min. BTPC (150 mg) and copper (I) iodide (25 mg) were added and the mixture was heated to 60°-70° under nitrogen for 1 h, cooled and evaporated in vacuo. Ether (175 ml) was added, the mixture filtered and evaporated in vacuo and the residue purified by FCC. Elution with ether followed by System C (19:1-92:8) gave the title compound as a pale yellow oil (3.79 g), t.l.c. (System C 17:3) Rf 0.55.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04996218 |
| Source dataset | uspto-grants-1991_02 |
| ORD ID | ord-927f729192e8411fb3c440a2fd8b46e0 |
| Source note | uspto-grants-1991_02 |