Ethanol → N-[2-[-4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-2-pyrimidinamine ethanedioate

HRID 1085867Notes

Reaction equation

HRID 1085867 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][CH2:11][CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH2:31])[CH2:25][CH2:24]1)[CH3:9].[C:32](=[O:35])([O-:34])O.[Na+].C([OH:39])C>>[C:11]([OH:10])(=[O:39])[C:32]([OH:34])=[O:35].[CH2:8]([O:10][CH2:11][CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][N:23]1[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][NH:31][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:28]1)[CH3:9]

Participants

5

Reactant 4

HCID 702EthanolHCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 199115154-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine

Product 1

HCID 131716499N-[2-[-4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-2-pyrimidinamine ethanedioateYield 64.3%

Procedure

A mixture of 1.26 parts of 2-chloropyrimidine, 3.6 parts of 4-[[3-(2-ethoxyethyl) -3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine, 1.1 parts of sodium hydrogen carbonate and 64 parts of ethanol was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (93:7 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 2-propanol. The product was filtered off and dried, yielding 3.8 parts (64.3%) of N-[2-[-4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazinyl]ethyl]-2-pyrimidinamine ethanedioate(1:2); mp. 175.3° C. (compound 105).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of dichloromethane and methanol (93:7 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-1c7fab3e127344f6baec7a2577502e1f
Source dataset
uspto-grants-1991_04
Patent number
US05011842

Reaction notes

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