Sodium Methoxide → 2-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

HRID 224884Notes

Reaction equation

HRID 224884 reaction equation
[N+:1]([NH:4][C:5]([NH2:7])=[NH:6])([O-:3])=[O:2].C[O-].[Na+].[CH:11]([CH:13]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C:14](OCC)=O)=[O:12]>CO>[N+:1]([NH:4][C:5]1[NH:7][C:11](=[O:12])[C:13]([CH2:19][C:20]2[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)=[CH:14][N:6]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12788663Ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionateHCID 86287517Nitroguanidine

Product 1

HCID 127838322-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nitroguanidine (4.7 g) was added to a solution of sodium methoxide (prepared from 1.15 g sodium) in methanol (50 ml) and the mixture was refluxed for 45 minutes. Ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionate (10.7 g) was added and the mixture was refluxed for 34 hours and evaporated to a residue. This residue was dissolved in water and the solution was extracted with chloroform (subsequently discarded). The aqueous solution was adjusted to pH 5 with acetic acid, and the solid which precipitated out was filtered off to give 2-nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone m.p. 183.5°-186°.

Workup

  1. temperaturethe mixture was refluxed for 45 minutes
  2. temperaturethe mixture was refluxed for 34 hours
  3. customevaporated to a residue
  4. dissolutionThis residue was dissolved in water
  5. extractionthe solution was extracted with chloroform (
  6. customthe solid which precipitated out
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-944765b5dd9940988899a8f51823c970
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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