Buchwald–Hartwig amination, record ord-cb91af3b3ac34425a6933ab18a143ee0
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)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate | C₁₃H₁₈BrNO₂ | |
| Reactant | 8-Chloro-6-pyridin-4-ylquinazolin-2-amine | C₁₃H₉ClN₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl N-[(1R)-1-[4-[(8-chloro-6-pyridin-4-ylquinazolin-2-yl)amino]phenyl]ethyl]carbamate | C₂₆H₂₆ClN₅O₂ | 50.96% |
Conditions
- Temperature
- 100 °C
Yield
- 51% of tert-butyl N-[(1R)-1-[4-[(8-chloro-6-pyridin-4-ylquinazolin-2-yl)amino]phenyl]ethyl]carbamate.
Procedure
Copied from the source record, unedited
A 250 mL roundbottom flask was charged with 8-chloro-6-(pyridin-4-yl)quinazolin-2-amine (EN01547-76-1; 3.09 g, 12.04 mmol), (R)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (EN01547-74-1; 4.42 g, 14.72 mmol), Pd2(dba)3 (114.4 mg, 2.1 mol % Pd), XantPhos (155.0 mg, 2.2 mol %), and Cs2CO3 (5.57 g, 17.10 mmol). The flask was evacuated and backfilled with N2 (3x), and then anhydrous dioxane (40 mL) was added. The mixture was allowed to stir at room temperature for ~5 minutes and was then heated under N2 in a 100 °C oil bath. After heating overnight, LC-MS showed complete conversion of the starting material to the desired product (trace N-phenylated product). A significant side product appeared to be present, derived from the starting aminoquinazoline that had undergone two Suzuki couplings in t
The source
This record comes from experimental reaction archive (ord-cb91af3b3ac34425a6933ab18a143ee0). Open the source and check it against what is on this page.
experimental reaction archive record ord-cb91af3b3ac34425a6933ab18a143ee0 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.