Buchwald–Hartwig amination, record ord-dd820c31fef4456fb96fcbe0cfbfed80
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-Bromobenzyl)morpholine | C₁₁H₁₄BrNO | |
| 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 | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Butyl Acetate | C₆H₁₂O₂ | |
| Product | 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-N-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine | C₂₄H₂₉FN₆O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-N-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
Tris(dibenzylideneacetone)dipalladium(0) (4.5 mg, 4.91 µmol) and 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (4.38 mg, 9.20 µmol) were dissolved in butyl acetate (1.8 mL) in a 10 mL Schlenk tube and activated at 100 °C for 6 min under argon. Then 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (51 mg, 0.18 mmol), 4-(4-bromobenzyl)morpholine (49.5 mg, 0.19 mmol) and Sodium tert-pentoxide (32.4 mg, 0.29 mmol) were added. It was degassed again and stirred at 100 °C under argon. The reaction was followed by HPLC. After 4.5 h no conversion was observed. Hence the whole reaction mixture was discarded.
The source
This record comes from experimental reaction archive (ord-dd820c31fef4456fb96fcbe0cfbfed80). Open the source and check it against what is on this page.
experimental reaction archive record ord-dd820c31fef4456fb96fcbe0cfbfed80 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.