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

HRID 1188722Notes

Reaction equation

HRID 1188722 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 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 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, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NMR (400 MHz, DMSO-d6) 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-a05614b9a485419b874cb011e03a94b7
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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