Reaction #1144429

Reaction equation

6-phenythiothymine

4-(t-butyldimethylsiloxy)-butyl-p-toluenesulphonate

potassium carbonate

→

target compound

Yield 4.1%

1-(4-hydroxybutyl) -6-phenylthiothymine

Yield 4.1%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Otherto react for 4 hours at 80° C
3. 3
   ConcentrationThe reaction mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONadded with methanol
5. 5
   Filtrationfiltered
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONadded with 20 ml of tetrahydrofuran and 1 ml of 1N hydrochloric acid
8. 8
   ConcentrationThe reaction mixture was concentrated under reduced pressure
9. 9
   Washeluted with 2% methanol/chloroform The eluate
10. 10
    Concentrationwas concentrated
11. 11
    Othercrystallized from acetone/hexane

Procedure

To 2 ml of dimethyl sulfoxide, 468 mg (2.0 mmol) of 6-phenythiothymine, 358 mg (1.0 mmol) of 4-(t-butyldimethylsiloxy)-butyl-p-toluenesulphonate and 276 mg (2.0 mmol) of potassium carbonate were added and heated to react for 4 hours at 80° C. The reaction mixture was concentrated under reduced pressure, added with methanol and filtered. The filtrate was concentrated under reduced pressure, added with 20 ml of tetrahydrofuran and 1 ml of 1N hydrochloric acid and stirred for 90 minutes. The reaction mixture was concentrated under reduced pressure and adsorbed on a silica gel column and eluted with 2% methanol/chloroform The eluate was concentrated and crystallized from acetone/hexane to obtain 12.0 mg of the target compound (Yield: 4%).

Source