HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-{4-[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate | HCID 16756990 | — |
| Reactant | 5-Chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine | HCID 21935749 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-{4-[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester | HCID 67072414 | 51.8% |
Reaction Steps
A solution of 350 mg (1 mmol) 5-chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 118G]), 235 mg (1 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 417 mg (1 mmol) cesium carbonate in 5 ml DMF was stirred for 3 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. After purification of the crude product by chromatography over silica gel with AcOEt/heptane 1:3, 283 mg of pure 2-{4-[4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester was isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115611B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-90b8e88239b34fb28431dc7ad0348747 |
| Source note | uspto-grants-2006_10 |