Carbon tetrabromide → 2-[4-(2-bromo-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 591761Notes

Reaction equation

O[CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:13][C:14](=[O:26])[C:15]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[N:18][C:16]=3[N:17]=2)=[CH:7][C:6]=1[CH3:27].C(Br)(Br)(Br)[Br:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:29][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:13][C:14](=[O:26])[C:15]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[N:18][C:16]=3[N:17]=2)=[CH:7][C:6]=1[CH3:27]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-pyrido[2,3-d]pyrimidin-4-one (0.50 g, 1.34 mmol) in anhydrous DMF (6 mL) was added carbon tetrabromide (0.53 g, 1.61 mmol) and triphenylphosphine (0.42 g, 1.61 mmol). The reaction mixture was stirred at 25° C. for 16 hours. DMF was removed under vacuum and dichloromethane (200 mL) was added. The organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous sodium sulfate. Solvent was removed and the residue was washed with ether (100 mL) to give 2-[4-(2-bromo-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-pyrido[2,3-d]pyrimidin-4-one as a white solid. Yield: 0.23 g (40%).

Workup

customDMF was removed under vacuum and dichloromethane (200 mL)
additionwas added
washThe organic phase was washed with water (100 mL)
dry with materialbrine (100 mL), and dried over anhydrous sodium sulfate
customSolvent was removed
washthe residue was washed with ether (100 mL)

Sources & evidence

ORD record: ord-70b4e534bf9b4936a194b5cc1a485c47
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238640B2

Reaction notes

Loading…