N-bromobutanimide → 4-[(5-Bromo-4,6-dichloropyrimidin-2-yl)amino]benzonitrile

HRID 1643350Notes

Reaction equation

HRID 1643350 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:18][C:7]1[C:6]([Cl:8])=[N:5][C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 467812514-[(4,6-Dichloropyrimidin-2-yl)amino]benzonitrile

Product 1

HCID 221700934-[(5-Bromo-4,6-dichloropyrimidin-2-yl)amino]benzonitrileYield 55.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2.11 g of 4-[(4,6-dichloro-2-pyrimidinyl)amino]benzonitrile (0.00796 mol) was added 500 ml of CHCl3 and the mixture was stirred for 30 minutes to allow the dissolution of almost all of starting compound. 1-bromo-2,5-pyrrolidinedione (0.0397 mol) was added in one portion and the reaction mixture was stirred at room temperature. After about 30 minutes, the mixture became a clear orange solution and the reaction became increasingly reddish with time. After 40 hours, TLC and HPLC/MS showed the reaction was complete. The reaction mixture was purified by flash silica gel column chromatography using CH2Cl2 as eluent. The fractions containing the desired product were isolated and the solvent evaporated. The residue was recrystallized from acetonitrile to afford 1.51 g of 4-[(5-bromo-4,6-dichloro-2-pyrimidinyl)amino]benzonitrile, yield 55% (intermediate 1).

Workup

  1. dissolutionthe dissolution of almost all of starting compound
  2. stirringthe reaction mixture was stirred at room temperature
  3. waitAfter about 30 minutes
  4. temperaturethe reaction became increasingly reddish with time
  5. waitAfter 40 hours
  6. customThe reaction mixture was purified by flash silica gel column chromatography
  7. additionThe fractions containing the desired product
  8. customwere isolated
  9. customthe solvent evaporated
  10. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b0f55fcc2819471687ff633bbfc25697
Source dataset
uspto-grants-2012_02
Patent number
US08119801B2

Reaction notes

Loading…