Sodium Carbonate → HCID 131716833, compound

HRID 1533963Notes

Reaction equation

HRID 1533963 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][N:13]([CH3:14])[C:7]2=[N:6][C:5]=1[CH3:15].[CH2:16]([O:18][CH2:19][CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[N:23]=[C:22]1[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH3:17].[C:37](=[O:40])([O-:39])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[C:9]([OH:10])(=[O:18])/[CH:4]=[CH:5]/[C:37]([OH:39])=[O:40].[CH2:16]([O:18][CH2:19][CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[N:23]=[C:22]1[CH2:30][N:31]1[CH2:32][CH2:33][N:34]([CH2:2][CH2:3][C:4]2[C:9](=[O:10])[N:8]3[CH:11]=[CH:12][N:13]([CH3:14])[C:7]3=[N:6][C:5]=2[CH3:15])[CH2:35][CH2:36]1)[CH3:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 19100910HCID 19100910, compoundHCID 19911564HCID 19911564, compound

Product 1

HCID 131716833HCID 131716833, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

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).

Workup

  1. temperatureat reflux temperature
  2. waitover weekend at room temperature
  3. customThe reaction mixture was evaporated
  4. extractionThe product was extracted with dichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. filtrationThe salt was filtered off
  14. customdried

Sources & evidence

ORD record
ord-9e9c456e02f245c3a46d3467665c491f
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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