Buchwald–Hartwig amination, record ord-1e88fef4eebd41feb29f461d3c9c5a57
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 | 2-Chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine | C₁₁H₇ClF₂N₂O | |
| Reactant | 3-(Methanesulfonylmethyl)aniline | C₈H₁₁NO₂S | |
| 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 | 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-[3-(methylsulfonylmethyl)phenyl]pyrimidin-2-amine | C₁₉H₁₇F₂N₃O₃S | 50.64% |
Conditions
- Temperature
- 100 °C
Yield
- 51% of 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-[3-(methylsulfonylmethyl)phenyl]pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (0.25 g, 0.97 mmol), 3-((methylsulfonyl)methyl)aniline (0.180 g, 0.97 mmol), cesium carbonate (1.270 g, 3.90 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.141 g, 0.24 mmol)and Pd2(dba)3 (0.178 g, 0.19 mmol) were suspended in degassed 1,4-dioxane (3 mL) at ambient temperature. The resulting mixture was degassed, purged with nitrogen and heated at 100 °C for 3 hours after which time reaction was shown to be complete by LC-MS. The mixture was allowed to cool overnight. The reaction mixture was diluted with water (250 mL), and extracted with DCM (250 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 50% ethyl
The source
This record comes from experimental reaction archive (ord-1e88fef4eebd41feb29f461d3c9c5a57). Open the source and check it against what is on this page.
experimental reaction archive record ord-1e88fef4eebd41feb29f461d3c9c5a57 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.