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

HRID 903363Notes

Reaction equation

HRID 903363 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-bccef702cf3b4d779ecb431689048ca6
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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