Sodium Carbonate → 1,7-dimethyl-1H,5H-imidazo[1,2 a]pyrimidin-5-one (E)-2-butenedioate

HRID 1708922Notes

Reaction equation

HRID 1708922 reaction equation
ClCC[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].C([O:18]CCN1C2=NC=CC=C2N=C1CN1CCNCC1)C.[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].[CH3:14][N:13]1[C:7]2=[N:6][C:5]([CH3:15])=[CH:4][C:9](=[O:10])[N:8]2[CH:11]=[CH:12]1

Participants

5

Reactant 3

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

Product 1

HCID 1317164981,7-dimethyl-1H,5H-imidazo[1,2 a]pyrimidin-5-one (E)-2-butenedioate

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 extracted 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-(3-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 extracted 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-a8620093ec044c35b797bd13616e956a
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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