Buchwald–Hartwig amination, record ord-20ba80f324544fc48cbce515702585f3
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 | 2-Chloropyrimidine | C₄H₃ClN₂ | |
| Reactant | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline | C₁₁H₁₃N₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]pyrimidin-2-amine | C₁₅H₁₅N₅O | 18.78% |
Conditions
- Temperature
- 100 °C
Yield
- 19% of N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
2-Chloropyrimidine (0.056 g, 0.49 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.100 g, 0.49 mmol), Palladium acetate (0.011 g, 0.05 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.017 g, 0.05 mmol) and Cesium carbonate (0.481 g, 1.48 mmol) were placed in a microwave vial. The mixture was capped and flushed with argon. 1,2-dimethoxyethane (5 mL) was added and the mixture was run in a microwave for 60 minutes at 100°C. Very little product. Added 0.1 eq ligand and palladium acetate, flushed with argon and run in the microwave at 100°C for 60 min. No change. Seems as if the 2-chloropyrimidine is not very soluble in DME. Added 1.5 mL DMF and the reaction was run again in the microwave for 60 minutes. The reaction mixture was filtrated through Celite and washed with dichloromethane. The
The source
This record comes from experimental reaction archive (ord-20ba80f324544fc48cbce515702585f3). Open the source and check it against what is on this page.
experimental reaction archive record ord-20ba80f324544fc48cbce515702585f3 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.