Buchwald–Hartwig amination, record ord-87f8e3ca7c9b4c4884d79136750f7a54
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | 2-Aminopyrimidine | C₄H₅N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-(4-chloro-2-pyridinyl)pyrimidin-2-amine | C₉H₇ClN₄ | 51.71% |
Conditions
- Temperature
- 100 °C
Yield
- 52% of N-(4-chloro-2-pyridinyl)pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (0.061 g, 0.27 mmol) was added to 2,4-dichloropyridine (0.500 g, 3.38 mmol), 2-Aminopyrimidine (0.321 g, 3.38 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.235 g, 0.41 mmol) and Cesium carbonate (2.202 g, 6.76 mmol) in dioxane (15 mL) at 20ºC under nitrogen. The resulting suspension was stirred at 100 °C for 90 minutes. Complete reaction by LCMS, cooled to room temperature. The reaction mixture was then filtered, washed with DCM and filtrate concentrated _in vacuo_ to give a yellow gum. This was then dissolved in DCM (200 mL), washed with water (200 mL) and brine (200 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0
The source
This record comes from experimental reaction archive (ord-87f8e3ca7c9b4c4884d79136750f7a54). Open the source and check it against what is on this page.
experimental reaction archive record ord-87f8e3ca7c9b4c4884d79136750f7a54 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.