Buchwald–Hartwig amination: 1-Fluoro-2-iodo-4-(trifluoromethyl)benzene → 5-bromo-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methoxypyrimidin-2-amine
0% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
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 | Tris(furan-2-yl)phosphane | C₁₂H₉O₃P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methoxypyrimidin-2-amine | C₁₂H₈BrF₄N₃O | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of 5-bromo-N-[2-fluoro-5-(trifluoromethyl)phenyl]-4-methoxypyrimidin-2-amine.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | Toluene | 100 °C | — | 81% |
| Tris(furan-2-yl)phosphane; Palladium (II) acetate | Cesium carbonate | Toluene | 90 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.513 g, 2.51 mmol), diacetoxypalladium (0.055 g, 0.245 mmol), tri(furan-2-yl)phosphine (0.126 g, 0.54 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.98 g, 3.38 mmol) and toluene (17 mL) under inert atmosphere. The reaction mixture was sealed and heated at 90 °C under 15h. The LCMS indicated no reaction ??? The sample discarded.
The source
This record comes from experimental reaction archive (ord-f903bfa68e6e46fb8291b98645969acd). Open the source and check it against what is on this page.
experimental reaction archive record ord-f903bfa68e6e46fb8291b98645969acd 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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