Sodium → 2-Nitroamino-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one

HRID 1719552Notes

Reaction equation

HRID 1719552 reaction equation
[Na].[N+:2]([NH:5][C:6]([NH2:8])=[NH:7])([O-:4])=[O:3].[CH:9]([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:20](=[O:29])[CH:19]=1)[C:12](OCC)=O)=[O:10]>CO>[N+:2]([NH:5][C:6]1[NH:8][C:9](=[O:10])[C:11]([CH2:17][C:18]2[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:20](=[O:29])[CH:19]=2)=[CH:12][N:7]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 20267140ethyl alpha-formyl-beta-(N-(2-dimethylaminoethyl)-2-oxo-4-pyridyl]propionateHCID 86287517Nitroguanidine

Product 1

HCID 703541452-Nitroamino-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-oneYield 39.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a stirred solution of sodium (2.94 g) in methanol (65 ml) was added nitroguanidine (11.81 g, containing 25% w/w water) and methanol (20 ml). The mixture was stirred at reflux for 60 minutes, and then a solution of ethyl α-formyl-β-(N-(2-dimethylaminoethyl)-2-oxo-4-pyridyl]propionate (25.05 g) in methanol (75 ml) was added dropwise over 90 minutes. The reaction mixture was stirred under reflux for a further 21 hours. The reaction mixture was evaporated under reduced pressure, dissolved in water (150 ml) and extracted with chloroform (3×35 ml). The combined chloroform extracts were washed with water (2×10 ml). The combined aqueous layer and aqueous washings were taken to pH 4 with glacial acetic acid. The solvent was then evaporated under reduced pressure and a solid by-product crystallised from ethanol. The mother liquors were evaporated and another crystallisation from ethanol gave a further solid by-product. The mother liquor was evaporated under reduced pressure to afford 2-nitroamino-5-[1-(2-dimethylaminoethyl)-2-oxopyridin-4-ylmethyl]pyrimidin-4-one (11.26 g) as an oil.

Workup

  1. temperatureat reflux for 60 minutes
  2. stirringThe reaction mixture was stirred
  3. temperatureunder reflux for a further 21 hours
  4. customThe reaction mixture was evaporated under reduced pressure
  5. dissolutiondissolved in water (150 ml)
  6. extractionextracted with chloroform (3×35 ml)
  7. washThe combined chloroform extracts were washed with water (2×10 ml)
  8. customThe solvent was then evaporated under reduced pressure
  9. customa solid by-product crystallised from ethanol
  10. customThe mother liquors were evaporated
  11. customanother crystallisation from ethanol
  12. customgave a further solid by-product
  13. customThe mother liquor was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c940acfbcc654b08a870593d41e1654c
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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