N-bromobutanimide → 7-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368989Notes

Reaction equation

HRID 368989 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:17]3[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[N:25][C:18]=3[N:19]([CH2:23][CH3:24])[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:14][CH:15]=1>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH:29]([C:26]1[CH:27]=[CH:28][C:17]2[C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([Cl:9])[CH:11]=3)=[N:21][C:20](=[O:22])[N:19]([CH2:23][CH3:24])[C:18]=2[N:25]=1)[CH3:30]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 6604918YM-976

Product 1

HCID 232844947-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-oneYield 61.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (8.94 g, 50.2 mmol) and 200 mg of 2,2'-azobis(isobutyronitrile) were added to a solution of 15.0 g (47.8 mmol) of 4-(3-chlorophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2(1H)-one in 150 ml of carbon tetrachloride, followed by heating under reflux for 3 hours. The reaction solution was again mixed with 1.28 g (7.17 mmol) of N-bromosuccinimide and 100 mg of 2,2'-azobis(isobutyronitrile), followed by heating under reflux for 1 hour. After cooling to room temperature, insoluble matter was removed by filtration, and the resulting filtrate was mixed with water and extracted with carbon tetrachloride. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 11.5 g of 7-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one in the form of crystals. The yield was 61%.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. custominsoluble matter was removed by filtration
  6. additionthe resulting filtrate was mixed with water
  7. extractionextracted with carbon tetrachloride
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter removing magnesium sulfate
  11. filtrationby filtration
  12. concentrationthe filtrate was concentrated under a reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-aad9a3d61462434686dc9c3bf979dd25
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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