4,6-Dichloropyrimidine → 4-Chloro-6-(methylsulfanyl)pyrimidine

4,6-Dichloropyrimidine (2.0 g, 13.42 mmol) was dissolved in THF (10 mL), treated with sodium thiomethoxide (0.988 g, 14.10 mmol) and the resulting mixture was stirred at room temperature under argon for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the desired product as a white solid (623 mg);

1. customThe solvent was removed under reduced pressure
2. customthe residue was partitioned between ethyl acetate and brine
3. customThe ethyl acetate layer was separated
4. customdried under magnesium sulfate
5. customevaporated under reduced pressure
6. customThe residue was purified by column chromatography (Biotage SP4)
7. washeluting with a gradient of 0-20% ethyl acetate and iso-hexane
8. additionProduct containing fractions
9. customevaporated under reduced pressure

ORD record

ord-aa9b7fc791ff485cb75de6ad834a38b9

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2