4,6-Dichloro-2-methylpyrimidine → HCID 86732069, compound

Participants

Reaction Conditions

Reaction Steps

In the reaction vessel 4,6-dichloro-2-methylpyrimidine (26.3 g, 161 mmol, 1.0 eq), potassium trifluoro(vinyl)borate (0.905 g, 4.03 mmol) cesium carbonate (97 g, 299 mmol, 2.0 eq) and butyldi-1-adamantylphosphine (2.89 g, 8.06 mmol 0.054 eq) were combined. This mixture was then evacuated and backfilled with nitrogen (3 times). Toluene (452 ml) and water (45 mL) were added to this flask. This mixture was purged with nitrogen for 20 min, then palladium acetate (0.905 g, 4.03 mmol, 0.027 eq) was added. Continue purged for 10 min, then heated at 100° C. for 2 h. The mixture was cooled, diluted with EtOAc (200 mL), washed with water (×200 mL), dried, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to give 4-chloro-2-methyl-6-vinylpyrimidine (4-1) as a white solid.

Provenance & Evidence