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

HRID 903365Notes

Reaction equation

HRID 903365 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 heated under reflux for 45 minutes. Ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionate (10.7 g) was added and the mixture was heated under reflux for 24 hours and evaporated to dryness. The residue was dissolved in water and the solution was extracted with chloroform. The residual aqueous solution was adjusted to pH 5 with acetic acid, and the solid which precipitated was filtered off to give 2-nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone, m.p. 183.5°-186°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 24 hours
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in water
  7. extractionthe solution was extracted with chloroform
  8. customthe solid which precipitated
  9. filtrationwas filtered off

Sources & evidence

ORD record
ord-ded73c8f062844228cdb9a968e78265c
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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