Buchwald–Hartwig amination, record ord-453f34fcdc374f919797959874dcc393
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 | 1-Fluoro-2-iodo-4-(trifluoromethyl)benzene | C₇H₃F₄I | |
| Reactant | 2-Amino-5-bromo-4-methoxypyrimidine | C₅H₆BrN₃O | |
| 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 | 5-bromo-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methoxypyrimidin-2-amine | C₁₂H₈BrF₄N₃O | 84.88% |
Conditions
- Temperature
- 100 °C
Yield
- 85% of 5-bromo-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methoxypyrimidin-2-amine.
Procedure
Copied from the source record, unedited
To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.520 g, 2.55 mmol), diacetoxypalladium (0.059 g, 0.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (151.8 mg, 0.26 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.89 g, 3.07 mmol) and toluene (17 mL) under inert atmosphare. The reaction mixture was sealed and heated at 90 °C under 16h. The LCMS indicated a complete conversion of the SM. The reaction mixture was partitioned between ethyl acetate and NH4Cl-solution. The organic layer was washed with NH4Cl-solution, brine dried over sodium sulphate, filtered and concentrated in vacuum to give a yellow gum. The oil dissolved in dichloromethane charged on silica 100g and purified by flash chromatography eluting with Ethyl acetate (0-80)
The source
This record comes from experimental reaction archive (ord-453f34fcdc374f919797959874dcc393). Open the source and check it against what is on this page.
experimental reaction archive record ord-453f34fcdc374f919797959874dcc393 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.