반응 #162602

반응 방정식

DIPEA

3-[2-chloro-6-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane

8-Oxa-3-azabicyclo[3.2.1]octane, HCl

8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride

triethylamine

→

title compound

수율 65.6%

3,3′-(6-(4-Nitrophenyl)pyrimidine-2,4-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

수율 65.6%

용매

ethyl acetate

dioxane

반응 조건

후처리

1. 1
   기타In a 100 mL round-bottomed flask was placed
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at 80° C. for 64 hours
4. 4
   세척washed
5. 5
   workup.DISSOLUTIONThe solids between the organic phase and aqueous phase were dissolved in dichloromethane
6. 6
   세척washed with saturated NaHCO3
7. 7
   건조The combined organic phases were dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    workup.ADDITIONThe crude product was added to a silica gel column
11. 11
    세척eluted with ethyl acetate in hexanes (10-40%)

실험 절차

In a 100 mL round-bottomed flask was placed 3-[2-chloro-6-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane (14, 110 mg, 0.32 mmol) in dioxane (5 ml). 8-Oxa-3-azabicyclo[3.2.1]octane, HCl (2, 0.15 g, 1 mmol) and triethylamine (0.28 ml, 2 mmol) were added. The mixture was stirred at 80° C. for 16 hours. DIPEA was added (0.3 mL) and stirring was continued at 80° C. for 64 hours. The reaction mixture was diluted with ethyl acetate and washed with sat NaHCO3. The solids between the organic phase and aqueous phase were dissolved in dichloromethane and washed with saturated NaHCO3. The combined organic phases were dried over MgSO4, filtered and concentrated. The crude product was added to a silica gel column and eluted with ethyl acetate in hexanes (10-40%) to give 89 mg of the title compound (0.21 mmol, 65%).

출처