Реакция #66608

Уравнение реакции

(4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol

triethylsilane

trifluoroacetic acid

→

4-chloro-5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidine

Выход 91.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter 2 hours the solution was concentrated in vacuo, 10% K2CO3
2. 2
   workup.ADDITIONwas added
3. 3
   Экстракцияextracted with CH2Cl2
4. 4
   ПромывкаThe combined organic layers were washed with brine
5. 5
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеPurification via flash chromatography (4:1 hexanes/ethyl acetate)

Методика

To a solution of (4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol (6.5 g, 17.6 mmol) in 200 mL CH2Cl2 was added triethylsilane (28.0 mL, 176 mmol) and trifluoroacetic acid (TFA) (70 mL, 881 mmol). After 2 hours the solution was concentrated in vacuo, 10% K2CO3 was added and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (4:1 hexanes/ethyl acetate) afforded 4-chloro-5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidine (5.60 g, 91%) as a clear oil.

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