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

HRID 387213Notes

Reaction equation

HRID 387213 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, 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-9e2500a13eb94ad295031c6bd9aeef84
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

Loading…