HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 131735889, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 53419964 | HCID 53419964 | — |
| Reactant | N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine | HCID 58456089 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131735889 | HCID 131735889 | 47.1% |
Reaction Steps
A mixture of N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (110 mg, 0.290 mmol), tert-butyl 2-(5-bromopyridin-2-yl)acetate (51.3 mg, 0.189 mmol), palladium(II) chloride (dppf) (28 mg, 0.038 mmol) and sodium carbonate (0.2 ml, 0.400 mmol, 2 M) in DMF (2 ml) was evacuated and purged with argon (3×), and then was irradiated in a microwave reactor for 10 minutes at 100° C. The mixture was filtered and purified on reversed phase HPLC to afford tert-butyl 2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetate (49.5 mg, 0.089 mmol). MS ESI calc'd. for C23H23F3N4O2 [M+H]+ 445. found 445.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376418B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-d07f0df3b683463e875dcf575f1397ff |
| Source note | uspto-grants-2016_06 |