Buchwald–Hartwig amination, record ord-0cc10dc98bd741d3bb43f77d99dd2224
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 | 4-Iodopyridine | C₅H₄IN | |
| Reactant | 2-Chloro-4-aminopyrimidine | C₄H₄ClN₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)- | C₃₂H₆₂FeP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-chloro-N-pyridin-4-ylpyrimidin-4-amine | C₉H₇ClN₄ | 45.34% |
Conditions
- Temperature
- 80 °C
Yield
- 45% of 2-chloro-N-pyridin-4-ylpyrimidin-4-amine.
Procedure
Copied from the source record, unedited
diacetoxypalladium (0.035 g, 0.15 mmol) was added to a mixture of 2-chloropyrimidin-4-amine (0.250 g, 1.93 mmol), 4-iodopyridine (0.396 g, 1.93 mmol), cesium carbonate (0.755 g, 2.32 mmol) and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.105 g, 0.19 mmol) in 1,4-dioxane (10 mL) and the reaction mixture stirred for 18 hours at 80 °C under nitrogen. EtOAc (50ml) was added to the reaction mixture and then the organics washed with water (3 x 50ml), brine (50ml) and then dried over MgSO4. The organics were then evaporated in vacuo to give the crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 2-chloro-N-(pyridin-4-yl)pyrimidin-4-amine (0.181 g,
The source
This record comes from experimental reaction archive (ord-0cc10dc98bd741d3bb43f77d99dd2224). Open the source and check it against what is on this page.
experimental reaction archive record ord-0cc10dc98bd741d3bb43f77d99dd2224 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.