Réaction #896

Équation de réaction

NaH

4-chloro-2-(methylthio)pyrimidine

3-(trifluoromethyl)phenol

→

phenoxide

2-methylthio-4-[3-(trifluoromethyl)phenoxy]pyrimidine

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONVII-1) (3.0 g, 0.0187 mol) was added
2. 2
   Températurethe mixture was refluxed for about 10 hours
3. 3
   AutreThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
4. 4
   Autreto separate an organic phase
5. 5
   LavageThe organic phase was washed with aqueous saturated sodium chloride
6. 6
   Séchagedried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   Autrerecrystallized from a methanol/water system
9. 9
   Autreto obtain the intermediate compound

Mode opératoire

In THF, a phenoxide was prepared from 3-(trifluoromethyl)phenol (4.54 g, 0.0187×1.5 mol) was mixed with NaH (1.12 g (ca. 60% in mineral oil), 0.0187×1.5 mol), and 4-chloro-2-(methylthio)pyrimidine (Compound No. VII-1) (3.0 g, 0.0187 mol) was added thereto and the mixture was refluxed for about 10 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, then recrystallized from a methanol/water system to obtain the intermediate compound.

Source