Methyl iodide → methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate

HRID 60441Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:11][C:12]([NH:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:13])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:21]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:11]([CH3:21])[C:12](=[O:13])[N:14]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-bromo-2-(3-(3-methoxy-3-oxopropyl)ureido)nicotinic acid (15 g, 43.5 mmol) in acetone (150 mL) was added K2CO3 (18 g, 130.4 mmol) followed by CH3I (18 mL, 263.1 mmol). The reaction was heated in a sealed flask at 40° C. for 24 h, cooled to RT, concentrated then diluted with EA (200 mL) and water (100 ml). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to a residue which was purified by chromatography PE/EA eluted with (10:1 to 2:1) to give methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate (5.1 g, 34.4% yield) as a white solid. LCMS: MH+ 342 and TR=1.266 min. Used without further purification.

Workup

temperaturecooled to RT
concentrationconcentrated
additionthen diluted with EA (200 mL) and water (100 ml)
washThe organic layer was washed with brine (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to a residue which
customwas purified by chromatography PE/EA
washeluted with (10:1 to 2:1)

Sources & evidence

ORD record: ord-5625c04ea2394e8788dc00f749dbfc67
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440972B2

Reaction notes

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