Potassium Carbonate → 2-((6-methyl-3-(methylthio)-5-oxo-1,2,4-triazin-4(5H)-yl)methyl)benzonitrile

HRID 240270Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([S:8][CH3:9])=[N:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br)#[N:18]>CN(C=O)C.O>[CH3:1][C:2]1[C:3](=[O:10])[N:4]([CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[C:17]#[N:18])[C:5]([S:8][CH3:9])=[N:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (5, 1.546 g, 9.85 mmol) in dry DMF (10 mL) at 0° C. was added K2CO3 (1.36 g, 9.85 mmol) and 2-cyanobenzylbromide (2.316 g, 11.82 mmol). The mixture was heated at 0° C. for 16 h. The mixture was diluted with water, and extracted with EtOAc (50 mL×3). The combined extracts were washed with brine, dried over MgSO4, and concentrated. This was purified by column chromatography on silica gel, and eluted with 20% to 50% ethyl acetate in petroleum ether and 1:1:2 petroleum ether-dichloromethane-ethyl acetate to provide 2-((6-methyl-3-(methylthio)-5-oxo-1,2,4-triazin-4(5H)-yl)methyl)benzonitrile (6). MS: m/z, 273 (100%, M+1), 295 (60%, M+23).

Workup

extractionextracted with EtOAc (50 mL×3)
washThe combined extracts were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThis was purified by column chromatography on silica gel
washeluted with 20% to 50% ethyl acetate in petroleum ether and 1:1:2 petroleum ether-dichloromethane-ethyl acetate

Sources & evidence

ORD record: ord-2f74ad3bff324c83904ae47df838ab92
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648073B2

Reaction notes

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