Sodium Hydroxide → HCID 21897288, compound

HRID 719979Notes

Reaction equation

HRID 719979 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[N:10][C:9]([C:12]2([CH3:19])[C:16](=[O:17])[NH:15][C:14](=[O:18])[NH:13]2)=[CH:8][N:7]=1)=O.[OH-].[Na+]>CO.C(OCC)(=O)C>[NH2:5][C:6]1[N:7]=[CH:8][C:9]([C:12]2([CH3:19])[NH:13][C:14](=[O:18])[NH:15][C:16]2=[O:17])=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21897277HCID 21897277, compound

Product 1

HCID 21897288HCID 21897288, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 2,2-dimethyl-N-[5-(4-methyl-2,5-dioxo-imidazolidin-4-yl)-pyrazin-2-yl]-propionamide (1.16 g, 4.0 mmol) in methanol (30 mL) was treated with a 1N aqueous sodium hydroxide solution (15 mL). The mixture was heated at 65° C. for 4 h and at 25° C. overnight. The mixture was concentrated in vacuo, and the residue was dried in vacuo overnight to give a crude solid. This solid material was suspended in a mixture of ethyl acetate and methanol (100 mL, 1:1) and gently heated. The mixture was filtered, and the filtrate was concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 1/9 to 3/7 methanol/ethyl acetate) afforded 5-(5-amino-pyrazin-2-yl)-5-methyl-imidazolidine-2,4-dione (841 mg, 100%) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was dried in vacuo overnight
  3. customto give a crude solid
  4. temperaturegently heated
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dda2a8b33a8e47de9747a91cd7364a82
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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