Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | HCID 68756140 | HCID 68756140 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86637302 | HCID 86637302 | 71.4% |
Reaction Steps
A mixture of 2,4-dichloropyrimidine (0.589 g, 0.00395 mol), 3-(tetrahydro-2H-pyran-4-yl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (1.30 g, 0.00392 mol), tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.0002 mol), and potassium phosphate (2.5 g, 0.012 mol) in 1,4-dioxane (10 mL, 0.1 mol) and water (1 mL, 0.06 mol) was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexanes, to provide the desired product (890 mg, 71.36%). LCMS (M+H) 318.3
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-5409d7bdf40744ed860e274d2bacd81c |
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| Source note | uspto-grants-2012_11 |
|---|