HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 57516475, compound
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 | 5-Bromo-2-chloroanisole | HCID 2769567 | — |
| Reactant | 2-Chloro-5-methylpyrimidin-4-amine | HCID 4302175 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57516475 | HCID 57516475 | 55.3% |
Reaction Steps
A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.50 g, 3.5 mmol), 4-bromo-1-chloro-2-methoxy-benzene (0.65 mL, 4.8 mmol), Pd2(dba)3 (0.17 g, 0.19 mmol), Xantphos (0.22 g, 0.38 mmol) and cesium carbonate (2.3 g, 7.1 mmol) was suspended in dioxane (20 mL) and heated at reflux under the argon atmosphere for 5 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes to 40% EtOAc/hexanes) to afford the title compound (0.55 g, 55%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528143B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-d72a3bb8c5a04f009aa82fe529dcfe56 |
| Source note | uspto-grants-2009_05 |