Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Chloro-4-(methylthio)pyrimidine | HCID 16427148 | — |
| Reactant | 1-[5-(3-Amino-5-methylphenyl)-2-thiazolyl]cyclobutanol | HCID 58456395 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67430661 | HCID 67430661 | 92% |
Reaction Steps
To a mixture of 2-chloro-4-(methylsulfanyl)pyrimidine (Intermediate 28, 500 mg, 3.11 mmol) and Intermediate 15 (810 mg, 3.11 mmol) in dioxane (15 mL) was added palladium(II) acetate (70 mg, 0.311 mmol), XantPhos (270 mg, 0.467 mmol) and cesium carbonate (2 g, 6.23 mmol). The mixture was degassed for 10 min and then heated at 85° C. for 16 h. After cooling to ambient temperature, the reaction mixture was filtered over celite and was washed with DCM/MeOH. After solvent removal, the residue was purified by column chromatography on silica gel (10 to 100% 10:1 ethyl acetate: methanol in hexanes) to afford 1-[5-(3-methyl-5-{[4-(methylsulfanyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclobutanol (1.1 g, 2.86 mmol, 92%). MS ESI: [M+H]+ m/z 385.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08551984B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-513877586961448cba28c84a49405bec |
|---|
| Source note | uspto-grants-2013_10 |
|---|
