Water → Ethyl [(4-bromo-2-pyrimidinyl)thio]acetate

HRID 7633Notes

Reaction equation

HRID 7633 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.O[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([S:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:30]=1.O>O1CCOCC1>[Br:20][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([S:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 178418869HCID 178418869, compound

Product 1

HCID 12056458Ethyl [(4-bromo-2-pyrimidinyl)thio]acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under argon, 52.5 g (0.20 mol) of triphenylphosphine are initially charged in 600 ml of dioxane, and 35.6 g (0.20 mol) of N-bromosuccinimide are added a little at a time, with cooling. The mixture is stirred at RT for 30 min. 8.6 g (0.04 mol) of ethyl [(4-hydroxy-2-pyrimidinyl)thio]acetate are then added and the mixture is heated at reflux for 45 min. A total of 2 l of water are added to the mixture, which is then extracted 3× with in each case 300 ml of methyl tert-butyl ketone. The organic phase is washed 2× with water and 1× with concentrated NaCl solution, dried over magnesium sulphate and concentrated. The residue is stirred in 60 ml of methyl tert-butyl ketone and filtered off. The mother liquor is concentrated and the residue is purified by silica gel chromatography (dichloromethane).

Workup

  1. temperaturewith cooling
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 45 min
  4. extractionis then extracted 3× with in each case 300 ml of methyl tert-butyl ketone
  5. washThe organic phase is washed 2× with water and 1× with concentrated NaCl solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. stirringThe residue is stirred in 60 ml of methyl tert-butyl ketone
  9. filtrationfiltered off
  10. concentrationThe mother liquor is concentrated
  11. customthe residue is purified by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-7527eb69678f4b00afc468a3bbc062ef
Source dataset
uspto-grants-2006_08
Patent number
US07087616B2

Reaction notes

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