Buchwald–Hartwig amination: 4-Iodopyridine → 2-chloro-N-pyridin-4-ylpyrimidin-4-amine
45% yield, run at 80 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.