Reaktion #528648

Reaktionsgleichung

Tetrahydro-1(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

4-trifluoromethylphenyl chloroformate

→

tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-(4-trifluoromethylphenoxycarbonyloxy)-2(1H)-pyrimidinone

Lösungsmittel

pyridine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis charged into a glass reaction vessel
2. 2
   Sonstigeequipped with a mechanical stirrer
3. 3
   workup.ADDITIONis slowly added
4. 4
   workup.ADDITIONAfter the addition
5. 5
   workup.STIRRINGis stirred for an additional period of about 20 minutes
6. 6
   Sonstigecompletion of the reaction
7. 7
   FiltrationAfter this time the reaction mixture is filtered
8. 8
   Sonstigeresulting in the formation of a precipitate
9. 9
   FiltrationThis precipitate is recovered by filtration
10. 10
    workup.DISSOLUTIONis dissolved in ether
11. 11
    WaschenThe ether solution is washed with dilute aqueous sodium carbonate
12. 12
    Trocknenis dried over anhydrous magnesium sulfate
13. 13
    Filtrationis filtered

Vorschrift

Tetrahydro-1(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole) dissolved in pyridine (80 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The solution is cooled to a temperature of about 10° C and 4-trifluoromethylphenyl chloroformate (0.06 mole) dissolved in pyridine (25 ml) is slowly added with stirring over a period of about 15 minutes. After the addition is completed, the reaction mixture is warmed to room temperature and is stirred for an additional period of about 20 minutes to ensure completion of the reaction. After this time the reaction mixture is filtered. The filtrate is then combined with water (100 ml) resulting in the formation of a precipitate. This precipitate is recovered by filtration and is dissolved in ether. The ether solution is washed with dilute aqueous sodium carbonate, is dried over anhydrous magnesium sulfate and is filtered. The filtrate is then stripped of ether to yield the desired product tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-(4-trifluoromethylphenoxycarbonyloxy)-2(1H)-pyrimidinone as the residue.

Quelle