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

HRID 1719138Notes

Reaction equation

HRID 1719138 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

(a)(i) Sodium (1.15 g) was dissolved in methanol (50 ml), and nitroguanidine (4.7 g) was added to the cooled solution. The mixture was refluxed for 45 minutes, ethyl 2-formyl-3-(3-pyridyl)propionate (9.3 g) was added portionwise and the mixture was refluxed for 45 hours and evaporated to dryness. Water was added to the residue and the mixture was extracted with chloroform. The 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 refluxed for 45 minutes
  2. temperaturethe mixture was refluxed for 45 hours
  3. customevaporated to dryness
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. customthe solid which was precipitated
  7. filtrationwas filtered off
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-ce621b9170334e63b8630b918d109927
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

Loading…