HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 6-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-5-methoxy-pyrimidin-4-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 6-Chloro-5-methoxypyrimidin-4-amine | HCID 78721 | — |
| Reactant | 4-(4-(4-Fluoro-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazol-2-yl)piperidine | HCID 86632021 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 6-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-5-methoxy-pyrimidin-4-ylamine | HCID 89442709 | 22% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A mixture of 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1h-imidazol-2-yl]-piperidine (40.00 mg; 0.12 mmol; 1.0 eq.), 6-chloro-5-methoxypyrimidin-4-amine (20.48 mg; 0.13 mmol; 1.05 eq.), potassium carbonate (33.78 mg; 0.24 mmol; 2.0 eq.) in DMSO (1.00 ml) in a microwave vial was heated at 150° C. for 2 h. LC-MS show ˜40% conversion and product eluted closely to the amine starting material. The reaction mixture was workup and the crude was purified by reverse phase pre-HPLC (Waters, acetonitrile/0.1% TFA in water) to yield desired product in 22% yield. LC-MS: (M+1=451, obsd.=451).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09145392B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-bbdad9acfed64556906b51da4852d509 |
| Source note | uspto-grants-2015_09 |