Sodium → N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramide

HRID 903362Notes

Reaction equation

HRID 903362 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:19]=[N:20][CH:21]=[CH:22][CH:23]=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:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:12][N:7]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 13505286Ethyl 2-formyl-3-(3-pyridyl)propionateHCID 86287517Nitroguanidine

Product 1

HCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (1.15 g) was dissolved in methanol (50 ml) and nitroguanidine (4.7 g) was added to the cooled solution. The mixture was heated under reflux for 45 minutes, ethyl 2-formyl-3-(3-pyridyl)propionate (9.3 g) was added portionwise and the mixture was heated under reflux for 45 hours and evaporated to dryness. Water was added to the residue and the mixture was extracted with chloroform. The residual aqueous phase was adjusted to pH 5 with acetic acid, and the solid which was precipitated was filtered off, washed and dried to give 2-nitroamino-5-(3-pyridylmethyl)-4-pyrimidone, m.p. 214.5°-216°, in 38% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 45 hours
  5. customevaporated to dryness
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with chloroform
  8. customthe solid which was precipitated
  9. filtrationwas filtered off
  10. washwashed
  11. customdried

Sources & evidence

ORD record
ord-923ee034fb5142a0b83064a9ea10b275
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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