N-bromobutanimide → 5-Bromo-4-(2-furyl)-2-pyrimidinylamine

HRID 747150Notes

Reaction equation

HRID 747150 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[N:7]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:13][C:11]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]([NH2:12])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 38049894-(2-Furyl)pyrimidin-2-amine

Product 1

HCID 185072635-Bromo-4-(2-furyl)-2-pyrimidinylamineYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-(2-furyl)-2-pyrimidinylamine (4.10 g, 25.4 mmol) in N,N-dimethylformamide (40 ml) was added N-bromosuccinimide (4.53 g, 25.5 mmol) at 2° C., followed by stirring as it was. After 6 hours, the reaction mixture was diluted with an aqueous saturated sodium bicarbonate solution (240 ml). The mixture was ice-cooled, and then the crystals were collected by filtration and washed with water, to give the title compound (5.10 g, 84%) as a pale brown solid.

Workup

  1. temperaturecooled
  2. filtrationthe crystals were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-868dea27a9774a6195697dd544213120
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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