Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2-Cyanophenylboronic acid | HCID 2734610 | — |
| Reactant | 5-[(4-Bromophenyl)methyl]-2-methyl-6-propyl-3-(tetrahydro-2H-pyran-4-yl)-4(3H)-pyrimidinone | HCID 57460916 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57460915 | HCID 57460915 | 83% |
Reaction Steps
A mixture of 5-(4-bromobenzyl)-2-methyl-6-propyl-3-(tetrahydro-2H-pyran-4-yl)pyrimidin-4(3H)-one (0.7 g), (2-cyanophenyl)boronic acid (0.36 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.07 g), 2 M aqueous sodium carbonate solution (1.5 mL) and 1,4-dioxane (15 mL) was stirred at 100° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.61 g, 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07998968B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-3d1206f6062d42cf9af899b7b8825082 |
|---|
| Source note | uspto-grants-2011_08 |
|---|