Buchwald–Hartwig amination, record ord-3df00475fe9d41898bd3503e3b2ed03d
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 | 5-Bromo-2-iodo-4-methoxypyrimidine | C₅H₄BrIN₂O | |
| Reactant | N-Ethylaniline | C₈H₁₁N | |
| Reagent | Sodium 2-methylbutan-2-olate | C₅H₁₁NaO | |
| 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-ethyl-4-methoxy-N-phenylpyrimidin-2-amine | C₁₃H₁₄BrN₃O | 70.78% |
Conditions
- Temperature
- 100 °C
Yield
- 71% of 5-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amine.
Procedure
Copied from the source record, unedited
5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - XantPhos (7.16 mg, 0.01 mmol) and sodium 2-methylbutan-2-olate (0.055 g, 0.50 mmol) and di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added to the reaction mixture. The vial was sealed and evacuated and flushed with nitrogen and then stirred at 100°C o/n. LC/MS showed product formation. The reaction mixture was cooled to rt and then filtered over celite. The crude product was diluted with 25 ml of DCM and then washed with sat. NaHCO3 followed by brine. The organic phase was dried over a phase separator and then concentrat
The source
This record comes from experimental reaction archive (ord-3df00475fe9d41898bd3503e3b2ed03d). Open the source and check it against what is on this page.
experimental reaction archive record ord-3df00475fe9d41898bd3503e3b2ed03d 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.