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

HRID 1905903Notes

Reaction equation

HRID 1905903 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 solution of sodium methoxide (from 0.161 g sodium) in methanol (20 ml). Dried nitroguanidine (0.729 g) was added over 5 minutes and the mixture was stirred and boiled under reflux overnight and evaporated to dryness. The residue was dissolved in water (50 ml) and the solution was extracted with chloroform (2×25 ml, discarded) and acidified to pH 5 with acetic acid. The solid which precipitated out was filtered off and recrystallised from methanol-acetic acid to give 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (0.5 g) m.p. 215°-216° (decomp.).

Workup

  1. temperatureunder reflux overnight
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionthe solution was extracted with chloroform (2×25 ml, discarded)
  5. customThe solid which precipitated out
  6. filtrationwas filtered off
  7. customrecrystallised from methanol-acetic acid

Sources & evidence

ORD record
ord-1bd0b51dc02f4ed2be69315d2cf2d31e
Source dataset
uspto-grants-1987_03
Patent number
US04649141

Reaction notes

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