Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Bis(adamantan-1-yl)(butyl)phosphane | HCID 11371790 | — |
| Reactant | Potassium cyclobutyl(trifluoro)borate(1-) | HCID 25105160 | — |
| Reactant | HCID 58539140 | HCID 58539140 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58539090 | HCID 58539090 | 8.6% |
Reaction Steps
To a microwave tube was added (4-(5-bromo-4-(methylamino)pyrimidin-2-ylamino)-3-methoxyphenyl)(morpholino)methanone (100 mg, 0.24 mmol), potassium cyclobutyltrifluoroborate (177 mg, 1.1 mmol), cesium carbonate (0.23 g, 0.71 mmol), toluene (2.9 mL) and water (0.3 mL). The mixture was degassed by nitrogen bubbling for 15 minutes. di-(1-adamantyl)-n-butylphosphine (19 mg, 0.053 mmol) and palladium acetate (2.6 mg, 0.026 mmol) was then added. The reaction was sealed and heated at 11° C. for 2 hours. The reaction mixture was filtered and concentrated. The crude product was purified by RP-HPLC to give the desire product (8.1 mg, 8.6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08802674B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-92fa1a4e6df44a86a23adce11a83c23d |
|---|
| Source note | uspto-grants-2014_08 |
|---|
