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

Temperature

100 °C

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.

1. customThis mixture was then evacuated
2. additionToluene (452 ml) and water (45 mL) were added to this flask
3. customThis mixture was purged with nitrogen for 20 min
4. customContinue purged for 10 min
5. temperatureThe mixture was cooled
6. additiondiluted with EtOAc (200 mL)
7. washwashed with water (×200 mL)
8. customdried
9. filtrationfiltered
10. customthe solvent was evaporated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)

ORD record

ord-3aeb263374054e189bf68511a865243e

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200001B2