Tetrahydrofuran → HCID 58312744, compound

HRID 1397006Notes

Reaction equation

HRID 1397006 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])[S: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])[S:14]/2)[CH:6]=[CH:5][N:4]=1)(=[O:21])=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 58312726HCID 58312726, compound

Product 1

HCID 58312744HCID 58312744, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (Z)-5-((2-(methylthio)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (5) (3.5 g, 13.82 mmol) in THF (100 mL, 0.13 M) was treated with a solution of oxone (25.8 g, 41.5 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)thiazolidine-2,4-dione (6) as a solid (2.48 g, 3.94 g theoretical, 63%). LC-MS m/z 286 (M+1).

Workup

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

Sources & evidence

ORD record
ord-7303527d66644a11812505072a238b25
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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