Reaction #1144430

Reaction equation

chloromethylmethylsulfide

6-phenylthiothymine

triethylamine

→

target compound

Yield 8.1%

1-(methylthiomethyl)-6-phenylthiothymine

Yield 8.1%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Otherto react for 22 hours at room temperature
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   Washeluted with chloroform
4. 4
   ConcentrationThe eluate was concentrated
5. 5
   Othercrystallized from ethyl acetate

Procedure

To 4 ml of dimethylformamide, 0.17 ml (2.0 mmol) of chloromethylmethylsulfide, 0.47 g (2.0 mmol) of 6-phenylthiothymine, 0.56 ml (2.0 mmol) of triethylamine were added and allowed to react for 22 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was adsorbed on a silica gel column and eluted with chloroform. The eluate was concentrated and crystallized from ethyl acetate to obtain 45 mg of the target compound (Yield: 8%).

Source