Water → 5-(Aminomethyl)pyrimidine-2,4(1H,3H)-dione

HRID 2211819Notes

Reaction equation

HRID 2211819 reaction equation
[N:1]([CH2:4][C:5]1[C:6](=[O:12])[NH:7][C:8](=[O:11])[NH:9][CH:10]=1)=[N+]=[N-].O.[H][H]>C(O)C.[Pd]>[NH2:1][CH2:4][C:5]1[C:6](=[O:12])[NH:7][C:8](=[O:11])[NH:9][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 219630275-(azidomethyl)-2,4(1H,3H)-pyrimidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 152185025-(Aminomethyl)pyrimidine-2,4(1H,3H)-dioneYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The solution of 5-(azidomethyl)-2,4(1H,3H)-pyrimidinedione (0.275 g, 1.64 mmol) in ethanol: water (25:5 ml) was degassed with nitrogen, palladium on carbon (5%) was added, reaction was charged with hydrogen (55 PSI) and shaken for 2 h. The reaction was filtered and concentrated to give the 5-(aminomethyl)-2,4(1H,3H)-pyrimidinedione (0.20 g, 85%) as a solid. MS found: (M+H)+=142.

Workup

  1. additionwas added
  2. customreaction
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-003b32cffb874c3296ecaabeed21de8b
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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