Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Pyrimidine, 2,4-dichloro-5-methyl- | HCID 74508 | — |
| Reactant | 3-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile | HCID 59420165 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86637289 | HCID 86637289 | 78% |
Reaction Steps
A mixture of 2,4-dichloro-5-methylpyrimidine (0.62 g, 3.8 mmol), 3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (1.0 g, 3.17 mmol), tetrakis(triphenylphosphine)palladium (200 mg, 0.2 mmol), and potassium phosphate (2.0 g, 9.6 mmol) in 1,4-dioxane (9 mL) and water (0.9 mL) was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, concentrated. The residue was purified on silica gel, eluting with 0 to 80% EtOAc-hexanes, to give the desired product (780 mg, 78%). LCMS (M+H) 316.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08309718B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-772610f42eec48f781d592eb9f011dac |
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| Source note | uspto-grants-2012_11 |
|---|