Buchwald–Hartwig amination, record ord-c1015abd205e430c801b5231e1cdfbf2
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-Amino-4-methylpyrimidine | C₅H₇N₃ | |
| 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)-4-methylpyrimidin-2-amine | C₁₀H₉ClN₄ | 57.73% |
Conditions
- Temperature
- 100 °C
Yield
- 58% of N-(4-chloro-2-pyridinyl)-4-methylpyrimidin-2-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 4-methylpyrimidin-2-amine (3.69 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (150 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 suspended in DCM, isolubles filtered off and drie
The source
This record comes from experimental reaction archive (ord-c1015abd205e430c801b5231e1cdfbf2). Open the source and check it against what is on this page.
experimental reaction archive record ord-c1015abd205e430c801b5231e1cdfbf2 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.