Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Amino-6-chloropyrimidine | HCID 238012 | — |
| Reactant | HCID 67389116 | HCID 67389116 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 67261970 | HCID 67261970 | 5.1% |
Reaction Steps
To a degassed solution of acetonitrile (4 mL) and water (1 mL) were added potassium carbonate (4 eq, 2.8 mmol), 3-(5-chloro-2-thienyl)-1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 eq, 0.7 mmol), 4-amino-6-chloropyrimidine (1.1 eq, 0.77 mmol) and 1,1′-bis(diphenylphosphinoferrocene)palladium(II)dichloride (0.1 eq, 0.07 mmol). The mixture was stirred at 130° C. in the microwave for 60 min. At room temperature, the mixture was filtered over celite and the filtrate was evaporated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 1:0 to 9:1) to afford 12 mg of 6-[3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazol-4-yl]pyrimidin-4-amine (5% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08685974B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-1bcb972693444429bbb8c6a0bbffe409 |
|---|
| Source note | uspto-grants-2014_04 |
|---|