Ethyl Bromide → 6-Bromo-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one

HRID 1188723Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:15](=[O:16])[NH:14][C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=1.[CH2:17](Br)[CH3:18]>CN(C)C=O>[Br:3][C:4]1[C:15](=[O:16])[N:14]([CH2:17][CH3:18])[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of NaH (60%, 0.15 g, 3.75 mmol) in anhydrous dimethylformamide (10 mL) was added 6-bromo-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.68 g, 2.50 mmol) at room temperature and the reaction was stirred at 50° C. for 0.5 h. The reaction mixture was cooled down to room temperature and ethyl bromide (0.22 mL, 0.32 g, 2.93 mmol) was added and stirred at 50° C. for 1.5 h. After completion, the mixture was poured onto ice water (10 g), and the white precipitate was filtered off to give 6-bromo-8-ethyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.57 g, 1.90 mmol, 76%). ESMS m/z 300 (M+H)+.

Workup

temperatureThe reaction mixture was cooled down to room temperature
stirringstirred at 50° C. for 1.5 h
additionAfter completion, the mixture was poured onto ice water (10 g)
filtrationthe white precipitate was filtered off

Sources & evidence

ORD record: ord-d6d9e9336d9c4b1299967c28c3e3ee53
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674095B2

Reaction notes

Loading…