Water → HCID 60204524, compound

HRID 2267402Notes

Reaction equation

HRID 2267402 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:13][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH2:22][N:23]4[C:27]([CH3:29])([CH3:28])[C:26](=[O:30])[NH:25][C:24]4=[O:31])[N:15]=3)=[C:11]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:10]=2)=[CH:4][CH:3]=1.[OH:38]OS([O-])=O.[K+].[OH2:44]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:9]2[S:13][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][CH2:22][N:23]4[C:27]([CH3:29])([CH3:28])[C:26](=[O:30])[NH:25][C:24]4=[O:31])[N:15]=3)=[C:11]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:10]=2)(=[O:38])=[O:44])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 60204525HCID 60204525, compound

Product 1

HCID 60204524HCID 60204524, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(2-(4-(5-(4-Fluorophenylthio)-3-phenylthiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (0.100 g, 0.188 mmol) was dissolved in acetone (3.0 mL) and treated with a solution of Oxone™ (0.346 g, 0.563 mmol) in H2O (1.5 mL). The reaction mixture was allowed to stir at ambient temperature overnight and then diluted with 10 mL H2O. The suspension was filtered and the precipitate washed with additional portions of H2O. The solid was air-dried and then purified by flash chromatography, eluted with 1-10% MeOH/dichloromethane to afford the product as a bright yellow solid. MS (M+H)+ 566.

Workup

  1. filtrationThe suspension was filtered
  2. washthe precipitate washed with additional portions of H2O
  3. customThe solid was air-dried
  4. custompurified by flash chromatography
  5. washeluted with 1-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-e7377b17ba3e4e599d1694d6402e8b24
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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