Buchwald–Hartwig amination, record ord-572b233d6c664fada44bd8d3bb48fc2f
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-(4-Bromo-3-fluorobenzyl)morpholine | C₁₁H₁₃BrFNO | |
| Reactant | 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine | C₁₃H₁₆FN₅O | |
| Reagent | Sodium 2-methylbutan-2-olate | C₅H₁₁NaO | |
| Catalyst | Triphenylphosphine | C₁₈H₁₅P | |
| Catalyst | Palladium | Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine | C₂₄H₂₈F₂N₆O₂ | 73% |
Conditions
- Temperature
- 110 °C
Yield
- 73% of 5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), Triphenylphosphine (0.038 mL, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 73 % conversion was achieved. The reaction was stopped and the mixture was discarded.
The source
This record comes from experimental reaction archive (ord-572b233d6c664fada44bd8d3bb48fc2f). Open the source and check it against what is on this page.
experimental reaction archive record ord-572b233d6c664fada44bd8d3bb48fc2f 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.