Sodium Sulfite → HCID 10906058, compound

HRID 1836199Notes

Reaction equation

HRID 1836199 reaction equation
C[Si]([I:5])(C)C.O[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[C:14]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([CH2:26][CH3:27])[CH:20]=2)[NH:13][C:12]1=[O:28].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[I:5][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[C:14]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([CH2:26][CH3:27])[CH:20]=2)[NH:13][C:12]1=[O:28]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 85247Trimethylsilyl iodideHCID 10448521HCID 10448521, compound

Product 1

HCID 10906058HCID 10906058, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trimethylsilyl iodide (19.4 g, 47 mmol) was added to a stirred solution of 3-(4-hydroxybutyl)-6-(3-ethyl-4-methylanilino)uracil (7.7 g, 24.3 mmol) in dry chloroform (300 ml). The reaction mixture was stirred at reflux for 12 h, until disappearance of starting material (TLC). A saturated solution of aqueous sodium sulfite was added to decolorize the brown-purple solution. After separation of layers, the aqueous solution was extracted with chloroform, and the combined organic extracts were reduced to about one fourth volume. The solid was filtered and washed with water and acetone to give 9.9 g (95%) of IB-EMAU.

Workup

  1. temperatureat reflux for 12 h, until disappearance of starting material (TLC)
  2. customAfter separation of layers
  3. extractionthe aqueous solution was extracted with chloroform
  4. filtrationThe solid was filtered
  5. washwashed with water and acetone
  6. customto give 9.9 g (95%) of IB-EMAU

Sources & evidence

ORD record
ord-2435af14ea414baeb497dde2642e9da0
Source dataset
uspto-grants-2004_08
Patent number
US06777420B2

Reaction notes

Loading…