Water → 3-Methyl-2-(methylthio)-4(3H)-pyrimidinone

Participants

Reaction Conditions

Reaction Steps

2-Methylthio-3H-pyrimidin-4-one (Step 1, 6.29 g, 44.2 mmol) was suspended in DMF (100 mL), cooled to 0° C., and additional DMF (50 mL) was added. Solid LiHMDS (9.58 g, 57.3 mmol) was added in one portion, and the reaction was stirred at 0° C. MeI (3.6 mL, 57.8 mmol) was added via syringe, and the reaction was warmed to RT and stirred for 20.75 h. At this time, the mixture was poured into 300 mL H2O and extracted exhaustively with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered, concentrated, and purified on silica gel (3:1→3:2→1:1 hexanes/EtOAc) to give the title compound. MS (ESI pos. ion) m/z: 157. Calc'd for C6H8N2OS: 156.04.

Provenance & Evidence