HCID 178481629, compound → 5-Amino-3-methyl-imidazolidine-2,4-dione

HRID 76335Notes

Reaction equation

HRID 76335 reaction equation
C([NH:8][C:9]1[C:10](=[O:16])[N:11]([CH3:15])[C:12](=[O:14])[N:13]=1)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:8][CH:9]1[NH:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]1=[O:16]

Participants

4

Reactant 1

HCID 178481629HCID 178481629, compound

Product 1

HCID 552819085-Amino-3-methyl-imidazolidine-2,4-dioneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 5-benzylamino-3-methyl-imidazole-2,4-dione (Example 1.3, Part B) (400 mg, 1.84 mmol) in ethanol/ethyl acetate (50 mL, 1:1) was added 10% Pd/C catalyst (195 mg, 0.18 mmol). The flask was evacuated and filled with hydrogen three times and then stirred at room temperature for 23 h. After this period, the reaction mixture was filtered through celite and the filtrate was evaporated to give the product as a colourless solid (214 mg, 90%), mp 122-125° C. δH (300 MHz, CD3CN) 6.31 (br s, 1H, NH), 4.68 (d, J 1.5 Hz, 1H, CH), 2.87 (s, 3H, CH3). δH (300 MHz, D2O) 4.95 (s, 1H, CH), 2.96 (s, 3H, CH3). δC (75 MHz, D2O) 175.6, 158.5, 64.0 (CH), 24.3 (CH3).

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen three times
  3. waitAfter this period
  4. filtrationthe reaction mixture was filtered through celite
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1c6b2ad161514a719e5e92b8e2e2bf2e
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

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