Phenacyl bromide → 2-phenylimidazo[1,2-a]pyrimidine

HRID 127349Notes

Reaction equation

HRID 127349 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O>C(O)C>[C:12]1([C:10]2[N:1]=[C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 79782-Aminopyrimidine

Product 1

HCID 2041492-phenylimidazo[1,2-a]pyrimidineYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.5 g of 2-aminopyrimidine (0.1 mole), 20 g of ω-bromoacetophenone (0.1 mole) and 200 ml of 95% ethanol is refluxed for three hours and then heated at 60° for an additional 12 hours with stirring. After cooling, the reaction product is condensed to a thick liquid by evaporating it in a rotary evaporator. The residue is mixed with 500 ml of methylene chloride and 100 ml of 3 N sodiumhydroxide solution. The mixture is stirred for 10 minutes and then separated in two layers in a separatory funnel. The lower layer (solvent) is collected, washed with 100 ml of water and then evaporated to dryness under reduced pressure. The residue is washed with 2-propanol on a glass filter and dried in vacuum to yield about 20 g of 2-phenylimidazo(1,2-a)pyrimidine, m.p. 200° to 202° C.

Workup

  1. temperatureis refluxed for three hours
  2. temperatureheated at 60° for an additional 12 hours
  3. temperatureAfter cooling
  4. customcondensed to a thick liquid
  5. customby evaporating it
  6. customin a rotary evaporator
  7. additionThe residue is mixed with 500 ml of methylene chloride and 100 ml of 3 N sodiumhydroxide solution
  8. stirringThe mixture is stirred for 10 minutes
  9. customseparated in two layers in a separatory funnel
  10. customThe lower layer (solvent) is collected
  11. washwashed with 100 ml of water
  12. customevaporated to dryness under reduced pressure
  13. washThe residue is washed with 2-propanol on a glass
  14. filtrationfilter
  15. customdried in vacuum

Sources & evidence

ORD record
ord-ede9d9776f1343119a97d52b842b7bd8
Source dataset
uspto-grants-1981_03
Patent number
US04255573

Reaction notes

Loading…