1,2-Dibromoethane → 6-bromo-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1676390Notes

Reaction equation

HRID 1676390 reaction equation
[Br:1][C:2]1[C:3](=[O:15])[NH:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24]Br>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:15])[N:4]2[CH2:23][CH2:24][N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 593534425-bromo-2-(phenylamino)pyrimidin-4(3H)-one

Product 1

HCID 673474496-bromo-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-2-(phenylamino)pyrimidin-4(3H)-one (0.082 g, 0.308 mmol) in DMF (8 mL) was added K2CO3 (0.043 g, 0.308 mmol) and 1,2-dibromoethane (0.029 ml, 0.339 mmol). The reaction was stirred at 60° C. overnight, cooled to room temperature and then partitioned between EtOAc and saturated NaCl. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by trituration with Et2O/CH2Cl2. The resulting solid was washed with Et2O, and the filtrate discarded. The solid was then dissolved with CH2Cl2/MeOH, concentrated and dried under vacuum. The product was obtained (75 mg; 83%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.05 (s, 1H), 7.75 (m, 2H), 7.42 (m, 2H), 7.15 (m, 1H), 4.18 (m, 4H). LRMS (ESI pos) m/e 292, 294 (M+, Br pattern).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between EtOAc and saturated NaCl
  3. customThe layers were separated
  4. extractionthe aqueous layer was re-extracted with EtOAc (1×)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by trituration with Et2O/CH2Cl2
  9. washThe resulting solid was washed with Et2O
  10. dissolutionThe solid was then dissolved with CH2Cl2/MeOH
  11. concentrationconcentrated
  12. customdried under vacuum
  13. customThe product was obtained (75 mg; 83%) as a white solid

Sources & evidence

ORD record
ord-0c0369ea53894a5ba4888fc0db0be4b6
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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