HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Toluene → 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Toluene | HCID 1140 | — |
| Edukt | Potassium Hydroxide | HCID 14797 | — |
| Edukt | 6-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine | HCID 11729102 | — |
| Edukt | 4-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride | HCID 22281976 | — |
| Katalysator | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| Lösungsmittel | Ammonium Chloride | HCID 25517 | — |
| Produkt | 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide | HCID 19689488 | — |
Reaktionsschritte
A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05728706 |
| Quelldatensatz | uspto-grants-1998_03 |
| ORD ID | ord-50229f9f65b24c3fbf8cc4093165ef6b |
| Quellennotiz | uspto-grants-1998_03 |