Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 86619883 | HCID 86619883 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59558786 | HCID 59558786 | — |
Reaction Steps
A mixture of methane sulfonamide (0.22 g), tris(dibenzylideneacetone)-dipalladium (0) (33 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (17 mg), cesium carbonate (0.58 g) and 4-chloro-2-[(2,3-difluorobenzyl)thio]-6-(methylthio)pyrimidine (the product of step i) (0.38 g) in dioxane (10 mL) was heated at 100° C. for 18 h. The mixture was cooled and saturated ammonium chloride was added and the resulting mixture extracted with EtOAc. The combined organic extracts were washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and evaporated. The residue was purified by reverse phase HPLC eluting with acetonitrile/aq. 0.1% TFA mixtures to give the title compound as a white solid. Yield: 30 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07838675B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-ea1efe1bf94645debd67ab575c763ac4 |
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| Source note | uspto-grants-2010_11 |
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