Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86636275 | HCID 86636275 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57962324 | HCID 57962324 | 25% |
Reaction Steps
To a mixture of N-{3-[2-(6-aminopyridin-2-yl)ethyl]phenyl}-2-chloro-5-fluoropyrimidin-4-amine dihydrochloride (35.0 mg, 0.084 mmol) and triethylamine (0.035 mL, 0.25 mmol) in a mixed solvent of 1,4-dioxane (0.70 mL) and N,N-dimethylformamide (0.70 mL) was added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.8 mg, 0.01 mmol), palladium acetate (2.3 mg, 0.01 mmol) and cesium carbonate (54.7 mg, 0.17 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 160° C. for 1 hour. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give a residue, which was purified by silica gel column chromatography to provide the desired product as a white powder (6.4 mg, 25%). LCMS for C17H15FN5 (M+H)+: m/z=308.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871753B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-fe9e0394d2324b28820ef44412f762a1 |
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| Source note | uspto-grants-2014_10 |
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