Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Pyridinamine, 5-iodo- | HCID 88579 | — |
| 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 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 118103325 | HCID 118103325 | — |
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 (1.29 g, 3.41 mmol), 5-iodopyridin-2-amine (500 mg, 2.27 mmol), PdCl2(dppf) (333 mg, 0.455 mmol) and sodium carbonate (2.27 ml, 4.55 mmol) in dioxane (9.10 mL) was heated to 100° C. for 16 hours. The reaction mixture was then filtered through a CELITE plug and washed with 1:1 DCM:methanol. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give N-[3-(6-aminopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine as a colorless solid. MS APCI calc'd for C17H15F3N5 [M+H]+ 346. found 346.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09376418B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-eaa8c7e21197425c8647d1e100d190a5 |
|---|
| Source note | uspto-grants-2016_06 |
|---|
