Pentanoic acid, 2-acetyl-4-methyl-, ethyl ester → 5-isobutyl-6-methyl-2-nitraminopyrimid-4(3H)-one

HRID 1764424Notes

Reaction equation

HRID 1764424 reaction equation
[N+:1]([NH:4][C:5]([NH2:7])=[NH:6])([O-:3])=[O:2].[Na].[CH2:9]([CH:13]([C:19]([CH3:21])=O)[C:14](OCC)=[O:15])[CH:10]([CH3:12])[CH3:11]>CO>[CH2:9]([C:13]1[C:14](=[O:15])[NH:6][C:5]([NH:4][N+:1]([O-:3])=[O:2])=[N:7][C:19]=1[CH3:21])[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 538758Pentanoic acid, 2-acetyl-4-methyl-, ethyl esterHCID 5360545SodiumHCID 86287517Nitroguanidine

Product 1

HCID 1363884225-isobutyl-6-methyl-2-nitraminopyrimid-4(3H)-oneYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nitroguanidine (53.1 g) was added to a solution of sodium (17.6 g) in methanol (500 ml). The mixture was heated under reflux for 45 minutes. Ethyl α-isobutylacetoacetate (95.0 g) was then added dropwise to the refluxing mixture over 30 minutes. Refluxing was continued for a further 61/2 hours. Most of the methanol was removed and the residue was dissolved in water. Unreacted β-keto-ester was removed by extraction with chloroform and the solution was acidified with concentrated hydrochloric acid. The separated solid was washed with water and dried, giving 5-isobutyl-6-methyl-2-nitraminopyrimid-4(3H)-one (formula IV, R1 = CH3, R = isobutyl) (73.2 g). A sample recrystallised from ethanol had a melting point of 179°-181° (decomp.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureRefluxing
  4. custom2 hours
  5. customMost of the methanol was removed
  6. dissolutionthe residue was dissolved in water
  7. customwas removed by extraction with chloroform
  8. washThe separated solid was washed with water
  9. customdried

Sources & evidence

ORD record
ord-94fe311ea68c439eb6a965b720b45c2c
Source dataset
uspto-grants-1978_09
Patent number
US04116674

Reaction notes

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