N-bromobutanimide → HCID 86697012, compound

HRID 400556Notes

Reaction equation

HRID 400556 reaction equation
[CH3:1][NH:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][C:7]=2[N:8]=1.[Al].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:11]1[C:10]([CH3:13])=[N:9][C:7]2[N:8]=[C:3]([NH:2][CH3:1])[N:4]=[CH:5][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 5359268AluminumHCID 86697013HCID 86697013, compound

Product 1

HCID 86697012HCID 86697012, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cool a solution of N,7-dimethylpyrido[2,3-d]pyrimidin-2-amine (6.73 g, 38.6 mmol) in acetonitrile (160 mL) in an ice bath and shield from light with aluminum foil. Add N-bromosuccinimide (6.88 g, 38.6 mmol) and stir at 0° C. for 2 h. Transfer the reaction to a 5° C. refrigerator for 4 days. Collect the solid by filtration. Wash the solid with DCM and concentrate the washings to obtain the title compound (3.0 g, 31% yield). MS (m/z): 253.0/255.0 (M+1).

Workup

  1. customthe reaction to a 5° C. refrigerator for 4 days
  2. customCollect the solid
  3. filtrationby filtration
  4. washWash the solid with DCM
  5. concentrationconcentrate the washings

Sources & evidence

ORD record
ord-3de32d780389411188adedeaa59a041d
Source dataset
uspto-grants-2014_06
Patent number
US08741911B2

Reaction notes

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