Buchwald–Hartwig amination, record ord-99e222e4d9a34b6bb8073fb91a88f0f7
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 | 3-Bromo-4-fluorobenzyl Alcohol | C₇H₆BrFO | |
| Reactant | 2-Chloro-4-aminopyrimidine | C₄H₄ClN₃ | |
| 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 | 1,4-Dioxane | C₄H₈O₂ | |
| Product | (3-(2-Chloropyrimidin-4-ylamino)-4-fluorophenyl)methanol | C₁₁H₉ClFN₃O | 0% |
Conditions
- Temperature
- 150 °C
Yield
- 0% of (3-(2-Chloropyrimidin-4-ylamino)-4-fluorophenyl)methanol.
Procedure
Copied from the source record, unedited
diacetoxypalladium (8.67 mg, 0.04 mmol) was added to 2-chloropyrimidin-4-amine (100 mg, 0.77 mmol), (3-bromo-4-fluorophenyl)methanol (158 mg, 0.77 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (53.6 mg, 0.09 mmol) and cesium carbonate (503 mg, 1.54 mmol) in 1,4-dioxane (4 mL) . The resulting suspension was stirred at 150 °C in the microwave for 30 minutes. None of the desired material was visible by LCMS. Reaction abandoned.
The source
This record comes from experimental reaction archive (ord-99e222e4d9a34b6bb8073fb91a88f0f7). Open the source and check it against what is on this page.
experimental reaction archive record ord-99e222e4d9a34b6bb8073fb91a88f0f7 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.