HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(5-ethyl-1-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl)thio]methyl}benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 178437208 | HCID 178437208 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(5-ethyl-1-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl)thio]methyl}benzonitrile | HCID 67775665 | 32.4% |
Reaction Steps
To a suspension of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(5-ethyl-4-oxo-1,4-dihydro-2-pyrimidinyl)thio]methyl}benzonitrile (120 mg, 0.258 mmol) and DIPEA (0.090 ml, 0.515 mmol) in DCM (2 mL) was added MeI (0.02416 ml, 0.386 mmol). The mixture was stirred at room temperature for 2 h. The reaction was then quenched with water, extracted with EA. The combined organic layers were dried with Na2SO4, filtered, concentrated and purified via reverse phase flash chromatography to afford the title compound (40 mg, 32.4% yield). LCMS: rt=3.44 min, [M+H+]=480
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-450586cc188543e5a04eb62486e7e865 |
| Source note | uspto-grants-2014_01 |