Réaction #897

Équation de réaction

Ethanol

NaH

m-trifluoromethyl-phenol

NaH

4,6-dichloro-2-methylthiopyrimidine

→

4-ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

Solvants

THF

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONVII-23)(5.0 g, 0.0256 mol) was added
2. 2
   workup.ADDITIONwere added
3. 3
   TempératureThe resulting solution was refluxed for about 7 hours
4. 4
   AutreThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
5. 5
   Autreto separate an organic phase
6. 6
   LavageThe organic phase was washed with aqueous saturated sodium chloride
7. 7
   Séchagedried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated
9. 9
   Autrepurified on a silica gel column

Mode opératoire

Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-trifluoromethyl-phenol (6.23 g, 0.0256×1.5 mol), NaH (1.54 g, (ca.60% in mineral oil), 0.0256×1.5 mol), and KI (2.12 g, 0.0256×0.5 mol) dissolved in DMF were added. The resulting solution was refluxed for about 7 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, and thereafter purified on a silica gel column.

Source