N-bromobutanimide → 3-Bromo-5-chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine

HRID 2171537Notes

Reaction equation

HRID 2171537 reaction equation
[Cl:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[Br:19][C:8]1[N:7]2[C:2]([Cl:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[CH:5][C:6]2=[N:10][CH:9]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 59312932HCID 59312932, compound

Product 1

HCID 593129203-Bromo-5-chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 mg (0.67 mmol) of 5-chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) are suspended in chloroform (30 ml), 238 mg (1.34 mmol) of N-bromosuccinimide are added, and the reaction mixture is stirred at RT for 12 h. The reaction mixture is diluted with ethyl acetate (100 ml) and water (75 ml), and the organic phase is separated off, dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is stirred with acetonitrile (20 ml) and then diethyl ether (20 ml), and the solid is filtered off with suction and dried. 103 mg (41% of theory) of the product are isolated.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in a rotary evaporator
  4. stirringThe residue is stirred with acetonitrile (20 ml)
  5. filtrationdiethyl ether (20 ml), and the solid is filtered off with suction
  6. customdried
  7. custom103 mg (41% of theory) of the product are isolated

Sources & evidence

ORD record
ord-9f01aeb199d1497b985e5b479aa23167
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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