Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate → 5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one

HRID 1248309Notes

Reaction equation

HRID 1248309 reaction equation
[CH:1]([CH:3]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[C:4](OCC)=O)=[O:2].C[O-].[Na+].[N+:20]([NH:23][C:24]([NH2:26])=[NH:25])([O-:22])=[O:21]>CO>[N+:20]([NH:23][C:24]1[NH:26][C:1](=[O:2])[C:3]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:4][N:25]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 3018359Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionateHCID 10942334Sodium MethoxideHCID 86287517Nitroguanidine

Product 1

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate (1.55 g) in methanol (20 ml) was added to a stirred solution of sodium methoxide (from 0.161 g sodium) in methanol (20 ml). Dried nitroguanidine (0.73 g) was added and the mixture was heated under reflux overnight and evaporated to dryness. The residue was dissolved in water (50 ml) and the solution was extracted with chloroform and the aqueous phase was adjusted to pH 5 with acetic acid. The solid which precipitated was filtered off and recrystallised from methanol-acetic acid to give 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (0.5 g, 27%), m.p. 215°-6° (decomp).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water (50 ml)
  5. extractionthe solution was extracted with chloroform
  6. customThe solid which precipitated
  7. filtrationwas filtered off
  8. customrecrystallised from methanol-acetic acid

Sources & evidence

ORD record
ord-ac8e7a81377d40bdad5bc27c15988d50
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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