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

HRID 1708923Notes

Reaction equation

HRID 1708923 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-piperazine-ethanamine, 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]-2pyrimidinamine 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-d238bf27c7004e5da868cce55311dad3
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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