HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium Carbonate → 2-(Methylsulfanyl)-4-[4-(methylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine | HCID 248063 | — |
| Edukt | 4-(Methylthio)phenylboronic acid | HCID 2733959 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Produkt | 2-(Methylsulfanyl)-4-[4-(methylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine | HCID 22018314 | 84% |
Reaktionsschritte
A mixture of 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (ButtPark Ltd, 2.86 g, 14.55 mmol), 4-(methylthio)phenylboronic acid (Aldrich, 2.83 g, 1.1 eq), tetrakistriphenylphosphine palladium (0) (0.2 g) and sodium carbonate (4.04 g, 2.6 eq) in DME (200 ml) and water (100 ml) was heated under reflux with stirring under N2 for 24 h. The reaction mixture was concentrated in vacuo and the resultant mixture partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo to a purple solid. Purification by flash column chromatography with cyclohexane:ethyl acetate as (6:1) as eluant gave the title compound as a yellow crystalline solid (3.869, 84%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07084148B2 |
| Quelldatensatz | uspto-grants-2006_08 |
| ORD ID | ord-32e67c2966e547bfa9726d4db0b83282 |
| Quellennotiz | uspto-grants-2006_08 |