HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-Chloro-5-methyl-N-(2,3-dimethylphenyl)pyrimidin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromo-o-xylene | HCID 68472 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Chloro-5-methylpyrimidin-4-amine | HCID 4302175 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Chloro-5-methyl-N-(2,3-dimethylphenyl)pyrimidin-4-amine | HCID 57516494 | — |
Reaction Steps
A mixture of 2-chloro-5-methylpyrimidin-4-amine (143.6 mg, 1 mmol), 1-bromo-2,3-dimethylbenzene (222 mg, 1.2 mmol), Pd2(dba)3 (92 mg, 0.1 mmol), Xantphos (174 mg, 0.3 mmol) and cesium carbonate (1.3 g, 4 mmol) were suspended in dioxane (150 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (10 mL) and added hexanes (100 mL). The solid was collected by filtration and washed with hexanes to afford the crude title compound as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604042B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-c5de136396a8413f9dd9ce06a6dd9095 |
| Source note | uspto-grants-2013_12 |