Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Cyclopropanecarboxamide | HCID 80376 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 4-Chloro-6-(4-nitrophenoxy)pyrimidine | HCID 14363850 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90020504 | HCID 90020504 | 46.2% |
Reaction Steps
Mix 4-chloro-6-(4-nitrophenoxyl)pyrimidine (10.6 g, 39.68 mmol), cyclopropanecarboxamide (8.7 g, 99.2 mmol) and 1,4-dioxane (150 mL). Then under N2, add tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 1.8 g, 1.98 mmol], (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 2.5 g, 3.97 mmol), Cs2CO3 (32 g, 99.5 mmol), and stir at 100° C. for 12 hrs. Cool to room temperature, filter, concentration and purification by chromatography (silica gel, DCM:EtOAc=1:5) afford the title compound (5.5 g, 43.6%). MS: (M+1): 301.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09359338B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-fe265f6ee938480b9a6ffa982fda3dcc |
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| Source note | uspto-grants-2016_06 |
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