Buchwald–Hartwig amination, record ord-484b31bdd1aa4746881181205ba1de67
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 | N'-[4-chloro-5-[[4-(cyanomethyl)phenyl]methyl]-6-methylpyrimidin-2-yl]-N,N-dimethylmethanimidamide | C₁₇H₁₈ClN₅ | |
| Reactant | (5S)-5-ethyl-1,3-oxazolidin-2-one | C₅H₉NO₂ | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| 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 | N'-[5-[[4-(cyanomethyl)phenyl]methyl]-4-[(5S)-5-ethyl-2-oxo-1,3-oxazolidin-3-yl]-6-methylpyrimidin-2-yl]-N,N-dimethylmethanimidamide | C₂₂H₂₆N₆O₂ | 45.7% |
Conditions
- Temperature
- 100 °C
Yield
- 46% of N'-[5-[[4-(cyanomethyl)phenyl]methyl]-4-[(5S)-5-ethyl-2-oxo-1,3-oxazolidin-3-yl]-6-methylpyrimidin-2-yl]-N,N-dimethylmethanimidamide.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (8.22 mg, 0.04 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (42.4 mg, 0.07 mmol) were added to dioxane (3 mL) and the solution was stirred at room temperature for 10 minutes.(E)-N'-(4-chloro-5-(4-(cyanomethyl)benzyl)-6-methylpyrimidin-2-yl)-N,N-dimethylformimidamide (240 mg, 0.73 mmol), (S)-5-ethyloxazolidin-2-one (169 mg, 1.46 mmol) and POTASSIUM CARBONATE (202 mg, 1.46 mmol) were added and the mixture was heated at 100 °C for 1 hour. The solvent was evaporated under reduced pressure and the crude product was purified by flash silica chromatography, elution gradient 2 to 5% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford (S,E)-N'-(5-(4-(cyanomethyl)benzyl)-4-(5-ethyl-2-oxooxazolidin-3-yl)-6-methylpyrimidin-2-yl)-N,N-dimet
The source
This record comes from experimental reaction archive (ord-484b31bdd1aa4746881181205ba1de67). Open the source and check it against what is on this page.
experimental reaction archive record ord-484b31bdd1aa4746881181205ba1de67 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.