HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Iodide → (4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine | HCID 21935960 | — |
| Reactant | Methyl [2-methyl-4-(methylamino)phenoxy]acetate | HCID 45097147 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | (4-{[4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester | HCID 67072224 | 64.8% |
Reaction Steps
To a solution of 400 mg (1.28 mmol) 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 27F]) and 268 mg (1.28 mmol) of (2-methyl-4-methylamino-phenoxy)-acetic acid methyl ester (example 5F]) in 8 ml of DMSO was added 194 mg (1.41 mmol) potasium carbonate and 192 mg (1.28 mmol) sodium iodide. The reaction mixture was stirred for 20 min at RT. It was then taken up in ether and washed with aqueous 10% KHSO4-solution (10%) and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:3, to give 403 mg of pure (4-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amino}-2-methyl-phenoxy)-acetic acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115611B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-a952df8a08c5490fafe1b7cc63321075 |
| Source note | uspto-grants-2006_10 |