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

A mixture of 4,6-dichloro-pyrimidine (20.93 g, 140 mmol) and sodium thiomethoxide (10.3 g, 147 mmol) in THF (100 mL) was stirred at room temperature for 16 h, then the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was separated and washed with brine, then dried over sodium sulfate and concentrated. The crude product residue was purified by recrystallization from hexanes (60 mL) to afford the title compound. The mother liquor was concentrated and the residue was purified by silica gel flash chromatography (0% to 10% ethyl acetate in hexanes as eluant) to afford additional title compound containing a small amount of byproduct 4,6-bis methylthio-pyrimidine. 1H NMR 400 MHz (CDCl3) δ 8.72 (s, 1H), 7.21 (s, 1H), 2.58 (s, 3H).

1. concentrationthe reaction mixture was concentrated
2. customThe residue was partitioned between ethyl acetate and brine
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe crude product residue was purified by recrystallization from hexanes (60 mL)

ORD record

ord-644a3c3ceece401ebfcb85cd9874ef97

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181238B2