Iodine chloride → 6-Chloro-5-iodopyrimidin-4-amine

Temperature

45 °C

To a solution of 3.03 g (23.39 mmol) of 6-chloropyrimidin-4-amine in 60 mL of dimethylformamide was added dropwise a solution of iodine monochloride (2.34 mL, 46.70 mmol) in 40 mL of dimethylformamide. Then the mixture was stirred at 45° C. overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between dichloromethane and a 4% aqueous solution of sodium bicarbonate. The organic layer was washed with water and brine, dried over magnesium sulphate, filtered and the solvent was removed in vacuum. The product was purified by flash chromatography (0% to 20%, methanol-dichloromethane) to obtain 4.28 g (72% yield) of the title compound.

1. customThe solvent was evaporated under reduced pressure
2. customthe residue was partitioned between dichloromethane
3. washThe organic layer was washed with water and brine
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customthe solvent was removed in vacuum
7. customThe product was purified by flash chromatography (0% to 20%, methanol-dichloromethane)

ORD record

ord-8ee1ac66138d4b39a5f3ea2a31b43c64

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388189B2