Buchwald–Hartwig amination, record ord-2a024728550642b2b2e2724a7387802d
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-Chloro-3-fluorobenzyl)morpholine | C₁₁H₁₃ClFNO | |
| Reactant | 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine | C₁₃H₁₆FN₅O | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| 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 | 9.15% |
Conditions
- Temperature
- 102 °C
Yield
- 9% 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
To degassed 1,4-dioxane (13.900 ml) in a flame-dried and argonflushed 50 mL roundbottomed flask were added 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (386 mg, 1.39 mmol) and 4-(4-chloro-3-fluorobenzyl)morpholine (320 mg, 1.39 mmol) followed by POTASSIUM TERT-BUTOXIDE (203 mg, 1.81 mmol) whilst stirring. The resulting slurry was flushed with argon followed by addition of TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (128 mg, 0.14 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (200 mg, 0.42 mmol), whereafter the dark violet reaction mixture was again flushed with argon and heated to 102 °C and stirred under argon for 15 h. The completion of the reaction was controlled by HPLC and the crude mixture was cooled to ambient temperatue
The source
This record comes from experimental reaction archive (ord-2a024728550642b2b2e2724a7387802d). Open the source and check it against what is on this page.
experimental reaction archive record ord-2a024728550642b2b2e2724a7387802d 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.