Buchwald–Hartwig amination, record ord-b814b75406f3451f844066ae5ac468ab
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 | (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine | C₁₄H₁₄ClN₃O | |
| Reactant | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline | C₁₁H₁₃N₃O | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine | C₂₅H₂₆N₆O₂ | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine.
Procedure
Copied from the source record, unedited
Purpose: to examine scale-up of microwave conditions established in a previous experiment. Charged a round-bottom flask with a mixture of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.702 g, 3.45 mmol), (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (1.0 g, 3.63 mmol), palladium (II) acetate (0.023 g, 0.10 mmol), rac-BINAP (0.108 g, 0.17 mmol), potassium carbonate (0.716 g, 5.18 mmol), and toluene (20 mL). The atmosphere s inerted through nitrogen purge cycles, then heated at 120 °C or 16 hours. HPLC-UV shows the reaction is not as clean as in the microwave, and conversion is very poor. The contents were allowed to continue heating over the weekend, but although conversion improved, the mixture contained many impurities. Not progressed. name='[Samples]
The source
This record comes from experimental reaction archive (ord-b814b75406f3451f844066ae5ac468ab). Open the source and check it against what is on this page.
experimental reaction archive record ord-b814b75406f3451f844066ae5ac468ab 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.