Urea → HCID 68283940, compound

HRID 1487184Notes

Reaction equation

HRID 1487184 reaction equation
[Na].[CH:2]([C:14]([O:16]CC)=O)([C:9]([O:11]CC)=O)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:19][C:20]([NH2:22])=[O:21]>C(O)C>[O:21]=[C:20]1[NH:22][C:9](=[O:11])[CH:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:14](=[O:16])[NH:19]1

Participants

5

Reactant 3

HCID 1176UreaHCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 5360545Sodium2×

Product 1

HCID 68283940HCID 68283940, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of anhydrous ethanol (1500 mL) was added sodium (25.2 g, 1.1 mol) in pieces. After all the sodium dissolved, triethyl ethane-1,1,2-tricarboxylate (180.0 g, 733 mmol) and urea (43.9 g, 733 mmol) was added respectively. The reaction mixture was heated at reflux overnight and cooled to room temperature, evaporated to dryness. The residue was diluted with water and acidified by diluted hydrochloric acid (2 N). The mixture was evaporated and purified by silica gel chromatography to afford the product ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)acetate as a pale-yellow solid (82.8 g, yield 35.0%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. additionThe residue was diluted with water
  5. customThe mixture was evaporated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a8e7c498d25a4efb9d03be8199c40fb8
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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