Diethyl Malonate → 1-(Prop-2-en-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione

HRID 1771117Notes

Reaction equation

HRID 1771117 reaction equation
[Na].[C:2]([O:10]CC)(=O)[CH2:3][C:4]([O:6]CC)=O.[CH2:13]([NH:16][C:17]([NH2:19])=[O:18])[CH:14]=[CH2:15]>C(O)C>[CH2:13]([N:16]1[C:2](=[O:10])[CH2:3][C:4](=[O:6])[NH:19][C:17]1=[O:18])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 11181AllylureaHCID 5360545Sodium

Product 1

HCID 2507141-(Prop-2-en-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trioneYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.2 g sodium thread (0.4 mol) was added to 300 mL anhydrous ethyl alcohol with stirring at room temperature. After the Na was dissolved completely, 30 mL diethyl malonate (0.2 mol) and 20 g allyl urea (0.2 mol) were added and refluxed for 5 hours. After the completion of reaction, sucking filtration was performed when the reaction solution was still hot. The filter cake was dissolved in 150 mL anhydrous ethyl alcohol and HCl was used to adjust the pH to 2˜3. After sucking filtration, the filtrate was left to stand for crystallization. After sucking filtration again, washing with anhydrous ethyl alcohol and drying, a white solid (19.5 g) was obtained. Yield: 58%, MS: 169 (M+1).

Workup

  1. temperaturerefluxed for 5 hours
  2. customAfter the completion of reaction
  3. filtrationfiltration
  4. dissolutionThe filter cake was dissolved in 150 mL anhydrous ethyl alcohol
  5. filtrationfiltration
  6. waitthe filtrate was left
  7. customto stand for crystallization
  8. filtrationfiltration again
  9. washwashing with anhydrous ethyl alcohol
  10. customdrying

Sources & evidence

ORD record
ord-01f5796632e949de9c0dee5574170eda
Source dataset
uspto-grants-2016_02
Patent number
US09249106B2

Reaction notes

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