HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 17881917, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Aminopyrimidine | HCID 7978 | — |
| Reactant | 2-Bromobenzaldehyde | HCID 81129 | — |
| Catalyst | Cesium carbonate | HCID 10796 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | HCID 12045512 | HCID 12045512 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 17881917 | HCID 17881917 | 64% |
Reaction Steps
A solution of 2-bromobenzaldehyde (0.35 mL, 3.0 mmol), 2-aminopyrimidine (0.34 g, 3.6 mmol), tris(dibenzylideneacetone)dipalladium (28 mg, 0.030 mmol), 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene (38 mg, 0.066 mmol) and cesium carbonate (28 mg, 0.030 mmol) in 1,4-dioxane (6.0 mL) was stirred at 100° C. for 19 hours under argon atmosphere. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=8/2) to obtain 2-(2-pyrimidylamino)benzaldehyde (0.38 g, 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07605272B2 |
| Source dataset | uspto-grants-2009_10 |
| ORD ID | ord-3e72590f51ca4d83a003b336d36e97b9 |
| Source note | uspto-grants-2009_10 |