N-bromobutanimide → 6-bromo-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1190930Notes

Reaction equation

HRID 1190930 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=[O:13])[NH:9][C:7]=2[N:8]=1.[Br:14]N1C(=O)CCC1=O>CN(C)C=O>[Br:14][C:11]1[C:10](=[O:13])[NH:9][C:7]2[N:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12347632-(methylthio)pyrido(2,3-d)pyrimidin-7(8H)-one

Product 1

HCID 221347206-bromo-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (6, 1.00 g, 5.2 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.6 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1×20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.5 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NMR (400 MHz, DMSO-d5) δ ppm 12.88 (br. s, 1H), 8.84 (s, 1H), 8.47 (s, 1H), 2.57 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe solid was triturated with hot water (1×20 mL)
  3. filtrationfiltered
  4. washwashed with isopropanol

Sources & evidence

ORD record
ord-2cef0b350f2240ca9d76b382a32655d4
Source dataset
uspto-grants-2014_03
Patent number
US08680099B2

Reaction notes

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