Buchwald–Hartwig amination: 2,6-Dimethylpiperazine → 5-chloro-N-[4-(3,5-dimethylpiperazin-1-yl)-2-methoxyphenyl]-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-amine
0% yield, run at 140 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | COc1cc(Br)ccc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1 | C₁₈H₁₃BrClN₅O | |
| Reactant | 2,6-Dimethylpiperazine | C₆H₁₄N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| 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 | 5-chloro-N-[4-(3,5-dimethylpiperazin-1-yl)-2-methoxyphenyl]-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-amine | C₂₄H₂₆ClN₇O | 0% |
Conditions
- Temperature
- 140 °C
Yield
- 0% of 5-chloro-N-[4-(3,5-dimethylpiperazin-1-yl)-2-methoxyphenyl]-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-amine.
Procedure
Copied from the source record, unedited
N-(4-bromo-2-methoxyphenyl)-5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine (107 mg, 0.25 mmol), 2,6-dimethylpiperazine (28.4 mg, 0.25 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.75 mg, 9.94 µmol), diacetoxypalladium (1.116 mg, 4.97 µmol) and cesium carbonate (162 mg, 0.50 mmol) were suspended in 1,4-dioxane (2 mL) . The reaction was purged with nitrogen and heated to 140 °C for 6 hours in an oil bath. Control LC/MS : no traces of expected product.
The source
This record comes from experimental reaction archive (ord-d5a89652aac64eea875d9bd85a60b6b2). Open the source and check it against what is on this page.
experimental reaction archive record ord-d5a89652aac64eea875d9bd85a60b6b2 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.
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