Triethylamine → 3-Bromo-2-(1-(2-(ethylsulfonyl)ethylamino)ethyl)-7-fluoro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1715037Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[N:5]=[C:6]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:7]2[C:8](=[O:11])[C:9]=1[Br:10])[CH3:3].C(N(CC)CC)C.[CH:24]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH2:25]>CO>[Br:10][C:9]1[C:8](=[O:11])[N:7]2[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:6]2=[N:5][C:4]=1[CH:2]([NH:1][CH2:25][CH2:24][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

E3 (222 mg, 0.78 mmol) was dissolved in 5 mL methanol. Triethylamine (0.11 mL, 0.78 mmol) was added followed by ethyl vinyl sulfone (0.082 mL, 0.78 mmol). The reaction was heated at 50° C. overnight. After removal of methanol, the mixture was purified by chromatography with 1:1 dichloromethane:ethyl acetate then gradient methanol in dichloromethane (2% to 4% to 6%) to give 318 mg E4 as an oil.

Workup

customAfter removal of methanol
customthe mixture was purified by chromatography with 1:1 dichloromethane

Sources & evidence

ORD record: ord-bd57d6bbaa714ef89b1769593a866b4c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799795B2

Reaction notes

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