N-bromobutanimide → HCID 18507285, compound

HRID 1356132Notes

Reaction equation

HRID 1356132 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15][CH3:16])[N:3]=1.[Br:17]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([Br:17])=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15][CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12451273HCID 12451273, compound

Product 1

HCID 18507285HCID 18507285, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 1.96 g (8.46 mmol) 2-amino-4-furan-2-yl-6-methylsulfanyl-pyrimidine-5-carbonitrile in 8 ml DMF was added dropwise a solution of 1.58 g (8.88 mmol) N-bromosuccinimide in 7 ml DMF and stirring continued at room temperature for 1 hour. The reaction mixture was then poured into 500 ml ice-water and the resulting precipitate collected by filtration and washed with water and then ether to afford 2.50 g (95%) 2-amino-4-(5-bromo-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a light brown crystalline solid. ES-MS m/e (%): 311 ([M{81Br}-H]−, 100), 309 ([M{79Br}-H]−, 95).

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-6596cc1afb9f42fabe2446667d90e87c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…