Buchwald–Hartwig amination: 2,4-Dichloropyridine → N-(4-chloro-2-pyridinyl)pyrimidin-2-amine

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

100 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

Copied from the source record, unedited

Palladium(II) acetate (0.061 g, 0.27 mmol) was added to 2,4-dichloropyridine (0.500 g, 3.38 mmol), 2-Aminopyrimidine (0.321 g, 3.38 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.235 g, 0.41 mmol) and Cesium carbonate (2.202 g, 6.76 mmol) in dioxane (15 mL) at 20ºC under nitrogen. The resulting suspension was stirred at 100 °C for 90 minutes. Complete reaction by LCMS, cooled to room temperature. The reaction mixture was then filtered, washed with DCM and filtrate concentrated _in vacuo_ to give a yellow gum. This was then dissolved in DCM (200 mL), washed with water (200 mL) and brine (200 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0

This record comes from experimental reaction archive (ord-87f8e3ca7c9b4c4884d79136750f7a54). Open the source and check it against what is on this page.

• experimental reaction archive record ord-87f8e3ca7c9b4c4884d79136750f7a54 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

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experimental reaction record.