5-Aminouracil → 5-amino-1,3-diazinane-2,4-dione

HRID 2211815Notes

Reaction equation

HRID 2211815 reaction equation
[NH2:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1>C(O)C>[NH2:1][CH:2]1[CH2:7][NH:6][C:5](=[O:8])[NH:4][C:3]1=[O:9]

Participants

3

Reactant 1

HCID 136115-Aminouracil

Product 1

HCID 4336775-amino-1,3-diazinane-2,4-dioneYield 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-aminouracil (0.3 g, 2.3 mmol) in ethanol: water (25:5 ml) was degassed with nitrogen gas, then palladium hydroxide on carbon was added. The reaction was charged with hydrogen (65 PSI). The reaction was shaken for 5 h, filtered to remove the catalyst and concentrated to give 5-aminodihydro-2,4(1H,3H)-pyrimidinedione (0.3 g, 100%) as a white solid. MS found: (M+H)+=130.

Workup

  1. customwater (25:5 ml) was degassed with nitrogen gas
  2. additionpalladium hydroxide on carbon was added
  3. additionThe reaction was charged with hydrogen (65 PSI)
  4. filtrationfiltered
  5. customto remove the catalyst
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c74182a616a54705ac1beeb152899efe
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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