Reaktion #41026

ord-fc016c9b3fec4379b34ff4bf91e99717

Reaktionsgleichung

ClCCCCBr
1-bromo-4-chloro-butane
O=C(c1ccccc1)n1c(=O)[nH]cc(I)c1=O
3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione
O=C([O-])[O-].[K+].[K+]
K2CO3
O
Water
ClCCCCBr
1-bromo-4-chloro-butane
O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O
title compound
Ausbeute 98.0%
O=C(c1ccccc1)n1c(=O)c(I)cn(CCCCCl)c1=O
3-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione
Ausbeute 98.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    Extraktionthe mixture was extracted with ethyl ether
  3. 3
    TrocknenThe organic phase was dried (Na2SO4)
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigeevaporated
  6. 6
    Sonstigethe crude was purified by flash chromatography with petroleum ether-ethyl acetate (7-3)

Vorschrift

3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep128, 2.5 g, 7.3 mmol), K2CO3 (1 g, 7.3 mmol) and 1-bromo-4-chloro-butane (1.26 ml, 10.95 mmol) were suspended in dry DMF (10 ml). After stirring the reaction at room temperature overnight, further 1-bromo-4-chloro-butane (840 μl, 7.3 mmol) was added. Water was added and the mixture was extracted with ethyl ether. The organic phase was dried (Na2SO4), filtered and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (7-3) to give the title compound as a white solid (3 g, 98% yield).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727988B2uspto-grants-2010_06