Buchwald–Hartwig amination, record ord-9a38e3cdbd7649cb80e5076ddc46669b
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 | 3-Bromo-2-methyl-5-nitropyridine | C₆H₅BrN₂O₂ | |
| Reactant | 4-(Pyridin-3-yl)pyrimidin-2-amine | C₉H₈N₄ | |
| 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 | Toluene | C₇H₈ | |
| Product | N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine | C₁₅H₁₂N₆O₂ | 18.86% |
Conditions
- Temperature
- 90 °C
Yield
- 19% of N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes. To this mixture was added 3-bromo-2-methyl-5-nitropyridine (694 mg, 3.20 mmol), then 4-(pyridin-3-yl)pyrimidin-2-amine (500 mg, 2.91 mmol) and cesium carbonate (1421 mg, 4.36 mmol), and the resulting mixture heated at 90 °C for 16 hours. The reaction mixture was cooled to RT, 50ml EtOAc was added and the mixture was filtered. The filtrate was concentrated, diluted with EtOAc (200 mL), and washed sequentially with water (150 mL) and saturated brine (150 mL). The organic layer was dried over MgSO4, f
The source
This record comes from experimental reaction archive (ord-9a38e3cdbd7649cb80e5076ddc46669b). Open the source and check it against what is on this page.
experimental reaction archive record ord-9a38e3cdbd7649cb80e5076ddc46669b 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.