Buchwald–Hartwig amination, record ord-69afe546f2d1404c8a01676e785a3836
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 | Isopropyl 4-[(6-chloro-5-methoxypyrimidin-4-yl)oxy]piperidine-1-carboxylate | C₁₄H₂₀ClN₃O₄ | |
| Reactant | 2-Methyl-6-(methylsulfonyl)pyridin-3-amine | C₇H₁₀N₂O₂S | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Bis[2-(diphenylphosphino)phenyl] ether | C₃₆H₂₈OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Isopropyl 4-((5-methoxy-6-((2-methyl-6-(methylsulfonyl)pyridin-3-yl)amino)pyrimidin-4-yl)oxy)piperidine-1-carboxylate | C₂₁H₂₉N₅O₆S | 49.95% |
Conditions
- Temperature
- 60 °C
Yield
- 50% of Isopropyl 4-((5-methoxy-6-((2-methyl-6-(methylsulfonyl)pyridin-3-yl)amino)pyrimidin-4-yl)oxy)piperidine-1-carboxylate.
Procedure
Copied from the source record, unedited
Bis[(2-diphenylphosphino)phenyl] ether (0.021 g, 0.04 mmol) was added in one portion to Palladium(II) acetate (4.33 mg, 0.02 mmol) in toluene (1 mL) (degassed by bubbling N2 through it for 30 minutes) at 20°C under nitrogen. After a few minutes a yellow suspension had formed. This added in one portion by pipette to a mixture of isopropyl 4-(6-chloro-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxylate (0.318 g, 0.96 mmol), 2-methyl-6-(methylsulfonyl)pyridin-3-amine (0.180 g, 0.96 mmol) and Sodium tert-butoxide (0.177 mL, 1.45 mmol) in toluene (3 mL) at 60°C under nitrogen. The resulting mixture was degassed using N2 / vacuum six times. The resulting suspension was stirred at 60 °C for 18 hours. Work up was by diluting with water (10 ml) and DCM (10 ml) then filtering through a pad of celite
The source
This record comes from experimental reaction archive (ord-69afe546f2d1404c8a01676e785a3836). Open the source and check it against what is on this page.
experimental reaction archive record ord-69afe546f2d1404c8a01676e785a3836 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.