Tetrahydrofuran → HCID 67371399, compound

HRID 1520124Notes

Reaction equation

HRID 1520124 reaction equation
CS[C:3]1[N:8]=[C:7](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[NH:14]/2)[CH:6]=[CH:5][N:4]=1.O[O:18][S:19]([O-:21])=O.[K+].[CH2:23]1COCC1>O>[CH3:23][S:19]([C:3]1[N:8]=[C:7](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[NH:14]/2)[CH:6]=[CH:5][N:4]=1)(=[O:21])=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 67373703HCID 67373703, compound

Product 1

HCID 67371399HCID 67371399, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (Z)-5-((2-(methylthio)pyrimidin-4-yl)methylene)imidazolidine-2,4-dione (5) (3.5 g, 14.83 mmol) in THF (100 mL, 0.15 M) was treated with a solution of oxone (27.35 g, 44.5 mmol, 3.0 equiv.) in water (175 mL). The resulting mixture was stirred at room temperature for 48 h. The resulting precipitate was filtered and washed with water (20 mL) and diethyl ether (20 mL) to afford (Z)-5-((2-(methylsulfonyl)pyrimidin-4-yl)methylene)imidazolidine-2,4-dione (6) as a solid (2.48 g, 3.97 g theoretical, 62%). LC-MS m/z 269 (M+1). The same procedure can be used with the N-benzyl (6b) and N-methyl (6c) analogs in comparable yields.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water (20 mL) and diethyl ether (20 mL)

Sources & evidence

ORD record
ord-077cec164a6e4b44b8402359fd76d5f9
Source dataset
uspto-grants-2015_07
Patent number
US09073903B2

Reaction notes

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