Urea → 5-(Butan-2-yl)pyrimidine-2,4,6(1H,3H,5H)-trione

HRID 992841Notes

Reaction equation

HRID 992841 reaction equation
[Na].[CH:2]([CH:6]([C:11]([O:13]C)=O)[C:7]([O:9]C)=O)([CH2:4][CH3:5])[CH3:3].[NH2:15][C:16]([NH2:18])=[O:17]>C(O)C>[CH:2]([CH:6]1[C:7](=[O:9])[NH:18][C:16](=[O:17])[NH:15][C:11]1=[O:13])([CH2:4][CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 1176UreaHCID 5360545SodiumHCID 184082881,3-Dimethyl 2-(1-methylpropyl)propanedioate

Product 1

HCID 2282815-(Butan-2-yl)pyrimidine-2,4,6(1H,3H,5H)-trioneYield 43.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

110 mL of anhydrous ethanol was reacted with 7.72 g of sodium metal. Subsequently 17.6 g (0.1 mol) of dimethyl secbutylmalonate was added, followed (after about 5 minutes) by urea (6.72 g). The reaction mixture was refluxed for 15 hours and 60 mL of ethanol was distilled off. 200 mL of water was added to the residue followed by 20 mL of concentrated sulfuric acid. Precipitated crystals were filtered off. The product was then recrystallized from water to yield 8 g of colorless crystals.

Workup

  1. custom(after about 5 minutes)
  2. temperatureThe reaction mixture was refluxed for 15 hours
  3. distillation60 mL of ethanol was distilled off
  4. addition200 mL of water was added to the residue
  5. customPrecipitated crystals
  6. filtrationwere filtered off
  7. customThe product was then recrystallized from water

Sources & evidence

ORD record
ord-7c3b6fcc29804eaba482e4b443da105d
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

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