반응 #1621145

반응 방정식

6-(2-chloroethyl)-1,7-dimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one

3-(2-ethoxyethyl)-2-(1-piperazinylmethyl)-3H-imidazo[4,5-b]pyridine

sodium carbonate

→

6-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]-pyridin-2-yl]methyl]1-piperazinyl]ethyl]-1,7-dimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one (E)-2-butenedioate

수율 47.3%

용매

4-methyl-2-pentanone

반응 조건

후처리

1. 1
   온도at reflux temperature
2. 2
   workup.WAITover weekend at room temperature
3. 3
   기타The reaction mixture was evaporated
4. 4
   추출The product was extracted with dichloromethane
5. 5
   세척The extract was washed with water
6. 6
   기타dried
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타The residue was purified by column chromatography over silica gel using
10. 10
    workup.ADDITIONa mixture of trichloromethane and methanol (90:10 by volume) as eluent
11. 11
    기타The pure fractions were collected
12. 12
    기타the eluent was evaporated
13. 13
    여과The salt was filtered off
14. 14
    기타dried

실험 절차

A mixture of 2.7 parts of 6-(2-chloroethyl)-1,7-dimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one, 2.9 parts of 3-(2-ethoxyethyl)-2-(1-piperazinylmethyl)-3H-imidazo[4,5-b]pyridine, 1.06 parts of sodium carbonate and 80 parts of 4-methyl-2-pentanone was stirred first for 44 hours at reflux temperature and then over weekend at room temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in 2-propanol. The salt was filtered off and dried, yielding 3.36 parts (47.3%) of 6-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]-pyridin-2-yl]methyl]1-piperazinyl]ethyl]-1,7-dimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one (E)-2-butenedioate(1:2); mp. 162.5° C. (compound 81).

출처