Реакция #417980

Уравнение реакции

diisopropyl azodicarboxylate

methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

triphenylphosphine

2-morpholin-4-ylethanol

→

methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураis cooled in an ice bath
2. 2
   workup.STIRRINGAfter stirring at room temperature for 2 hours
3. 3
   Другоеthe reaction mixture is evaporated in vacuo
4. 4
   СушкаThe organic phase is dried over sodium sulfate
5. 5
   Другоеevaporated
6. 6
   ДругоеThe residue is recrystallised from isopropanol
7. 7
   Другое2.06 min (method A)

Методика

A solution, kept under nitrogen, of 10.1 g (44 mmol) of methyl 3-(5-hydroxypyrimidin-2-yl)benzoate, 17.3 g (66 mmol) of triphenylphosphine and 5.9 ml (48.4 mmol) of 2-morpholin-4-ylethanol in 100 ml of THF is cooled in an ice bath, and 12.95 ml (66 mmol) of diisopropyl azodicarboxylate are slowly added dropwise with stirring. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo. The residue is taken up in 100 ml of dichloromethane and 100 ml of water. The organic phase is dried over sodium sulfate and evaporated. The residue is recrystallised from isopropanol: methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate as beige crystals; m.p. 89-91°; ESI 344 (M+H); HPLC: 2.06 min (method A).

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