Methyl iodide → 2-(Methylthio)-1H-pyrimidin-4-one

Temperature

0 °C

2-Thiouracil (33.3 g, 0.26 mol) was dissolved in an aqueous solution of sodium hydroxide (20.8 g in 183 mL of water; ˜0.52 mol). The mixture was placed in an ice bath until the internal reaction temperature was 0° C. Methyl iodide (18.5 mL, 0.29 mol) was slowly added. The resulting reaction mixture was allowed to return to room temperature and then stirred for 16 hours. The pale yellow solution was cooled to 0° C. and acidified with glacial acetic acid. The white precipitate that formed was collected by vacuum filtration, washed with cold water (3×150 mL), and dried to afford 2-methylsulfanyl-3H-pyrimidin-4-one as a white powder. (37.4 g, 98%).

1. customThe mixture was placed in an ice bath until the internal reaction temperature
2. customwas 0° C
3. customThe resulting reaction mixture
4. customto return to room temperature
5. customThe white precipitate that formed
6. filtrationwas collected by vacuum filtration
7. washwashed with cold water (3×150 mL)
8. customdried

ORD record

ord-6c2d46f176f2432f83d640b6dcf547d5

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217794B2