Buchwald–Hartwig amination, record ord-5cced2257316472bbbfef637f32f12c1
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-(1H-1,2,4-triazol-1-yl)pyridin-3-amine | C₈H₉N₅ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-[5-Methoxy-6-(2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ylamino)-pyrimidin-4-yloxy]-piperidine-1-carboxylic Acid Isopropyl Ester | C₂₂H₂₈N₈O₄ | 48.49% |
Conditions
- Temperature
- 90 °C
Yield
- 48% of 4-[5-Methoxy-6-(2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ylamino)-pyrimidin-4-yloxy]-piperidine-1-carboxylic Acid Isopropyl Ester.
Procedure
Copied from the source record, unedited
Sodium tert-butoxide (8.28 mL, 67.61 mmol) was added portionwise to a mixture of 2-methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-amine (4.94 g, 28.17 mmol) isopropyl 4-(6-chloro-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxylate (9.29 g, 28.17 mmol) and in dioxane (136 mL) at 18°C over a period of 1 minute under nitrogen. The mixture was degassed by subjecting to vacuum then nitrogen atmosphere (six times). Palladium(II) acetate (0.063 g, 0.28 mmol) and 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo{3.3.3}undecane (0.200 mL, 0.56 mmol) was added and the mixture degassed again. The resulting suspension was stirred at 90 °C for 3 hours. Palladium(II) acetate (0.126 g, 0.56 mmol) and 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo{3.3.3}undecane (0.400 mL, 1.12 mmol) was added and the
The source
This record comes from experimental reaction archive (ord-5cced2257316472bbbfef637f32f12c1). Open the source and check it against what is on this page.
experimental reaction archive record ord-5cced2257316472bbbfef637f32f12c1 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.