N-bromobutanimide → HCID 58603291, compound

HRID 502666Notes

Reaction equation

HRID 502666 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Br:17]N1C(=O)CCC1=O.C([O-])(=O)C.[K+]>CN(C)C=O>[Br:17][C:9]1[O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 517044Potassium AcetateHCID 58603253HCID 58603253, compound

Product 1

HCID 58603291HCID 58603291, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-amino-5-phenylfuro-[2,3-d]pyrimidine (2.3 g, 10.8 mmol) dissolved in dimethylformamide (100 mL) was added N-bromosuccinimide (2.0 g, 11.2 mmol) and potassium acetate (1.1 g, 11.2 mmol). The resulting solution was stirred overnight at room temperature. The mixture was then partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography (25% acetone/hexane) to give the product as a pale solid (2.0 g, 64%).

Workup

  1. customThe mixture was then partitioned between ethyl acetate (150 mL) and water (150 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography (25% acetone/hexane)

Sources & evidence

ORD record
ord-f1a449ea279749fc95f38863cfb318c1
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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