Buchwald–Hartwig amination: 3-Bromo-2-methyl-5-nitropyridine → N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)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

90 °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 (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes, then cooled to r.t. To this mixture at r.t was added 3-bromo-2-methyl-5-nitropyridine (694 mg, 3.20 mmol), then 4-(pyridin-3-yl)pyrimidin-2-amine (500 mg, 2.91 mmol) and cesium carbonate (1421 mg, 4.36 mmol), and the resulting mixture heated at 90 °C for 16 hours under N2. The reaction mixture was cooled to RT, 150ml EtOAc was added and the mixture was filtered. The filtrate was concentrated, diluted with EtOAc (500 mL), and washed sequentially with water (300 mL) and saturated brine (150 mL). The o

This record comes from experimental reaction archive (ord-93068c36902748b0a097205076445ea2). Open the source and check it against what is on this page.

• experimental reaction archive record ord-93068c36902748b0a097205076445ea2 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.