Реакция #643782

Уравнение реакции

NaH

3-(methylthio)-1-propanol

product

8-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methane-sulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

→

title compound

8-(2,6-Difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-(3-methylsulfanylpropoxy)-8H-pyrido[2,3-d]pyrimidin-7-one

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   ДругоеMost of the excess 3-(methylthio)-1-propanol was removed in vacuo
3. 3
   Другоеthe residue partitioned between EtOAc and H2O
4. 4
   ПромывкаThe organic phase was washed with H2O
5. 5
   Сушкаdried over anhyd Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated
8. 8
   Другоеto give the crude product
9. 9
   ПромывкаFlash chromatography eluted with 10-30% EtOAc/hexane
10. 10
    Другоеfollowed by recrystallization from CH2Cl2/hexane

Методика

NaH (12 mg, 0.5 mmol) was added to 3-(methylthio)-1-propanol (0.5 mL) and the mixture was stirred under Ar at 23°. After 5 min, gas evolution ceased, and the product of Example 48 (223 mg, 0.5 mmol) was added in a single portion. The mixture was stirred for 30 minutes. Most of the excess 3-(methylthio)-1-propanol was removed in vacuo, and the residue partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography eluted with 10-30% EtOAc/hexane, followed by recrystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. mp 127-128°, LC MS m/z=472 (MH+) Retention time=2.47 min.

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