Methyl iodide → 1-Butyl-3-hydroxy-4-methylpyridine-2-thione

To a solution of 1-butyl-3-hydroxy-4(N,N-dimethylaminomethyl)pyridine-2-thione (2-034-05) (1.0 g) in methylene chloride (20 mL) was added iodomethane (2.1 g) at room temperature. After the reaction mixture was stirred for 1 h, the solvent was evaporated under reduced pressure. To the residue were added ethanol (20 mL) and triphenylphosphine (1.6 g), and the reaction mixture was stirred at 75° C. for 20 h, and evaporated under reduced pressure. To the residue were added methanol (10 mL) and 1 mol/L aqueous sodium hydroxide solution (8 mL), and the reaction mixture was stirred at 60° C. for 2 h, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (toluene/acetone=4/1) to give 1-butyl-3-hydroxy-4-methylpyridine-2-thione (2-034-06) (0.57 g, 70%) as an oil.

1. customthe solvent was evaporated under reduced pressure
2. additionTo the residue were added ethanol (20 mL) and triphenylphosphine (1.6 g)
3. stirringthe reaction mixture was stirred at 75° C. for 20 h
4. customevaporated under reduced pressure
5. additionTo the residue were added methanol (10 mL) and 1 mol/L aqueous sodium hydroxide solution (8 mL)
6. stirringthe reaction mixture was stirred at 60° C. for 2 h
7. customevaporated under reduced pressure
8. customThe crude product was purified by silica gel column chromatography (toluene/acetone=4/1)

ORD record

ord-5e65d1e1a22f4518823b648257c2eea3

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06977266B2