Реакция #897

Уравнение реакции

Ethanol

NaH

m-trifluoromethyl-phenol

NaH

4,6-dichloro-2-methylthiopyrimidine

→

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

Растворители

THF

DMF

Условия реакции

Обработка

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

Методика

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.

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