HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 58748738, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Nitropyrimidin-2-amine | HCID 76490 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 5-Bromo-pyridine-2-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide | HCID 58748728 | — |
| Catalyst | Tris(dibenzylideneacetone) dipalladium | HCID 9832798 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 58748738 | HCID 58748738 | 35% |
Reaction Steps
In a dry 50 mL round bottom flask 5-nitro-pyrimidin-2-ylamine (0.2 g, 1.36 mmol), intermediate 21 (Example 29) (0.61 g, 2.04 mmol), cesium carbonate (1.33 g, 4.08 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.157 g, 0.272 mmol) and tris(dibenzylideneacetone) dipalladium (0.124 g, 0.136 mmol) were combined. Reactants were flushed with argon, diluted with dioxane (8 mL) and outfitted with reflux condenser. Reaction was heated to reflux for 18 h. Reaction was then filtered hot and solvents were evaporated to provide dark solids. Silica gel chromatography (6:1 DCM/MeOH) provided desired product as a yellow powder (0.17 g, 33% yield). Rf=0.23 (10% MeOH/DCM)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030487B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-4a63c764458a40a0ab0ce8cbf5ba8b32 |
| Source note | uspto-grants-2011_10 |