Benzenesulfinic acid, sodium salt → 5-Benzenesulfonyl-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester

HRID 1944449Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10](Br)=[CH:9][N:8]=[C:7]([S:12][CH3:13])[N:6]=1)=[O:4].[Na+].[C:15]1([S:21]([O-:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])=[CH:9][N:8]=[C:7]([S:12][CH3:13])[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 5-bromo-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester (2.3 g), benzenesulfinic acid sodium salt (1.9 g) and dimethyl sulfoxide (35 mL) was treated with bis[copper(I)triflate]benzene complex (3.3 g), and the resulting mixture was stirred at 65° C. for 1.5 hours. The mixture was cooled to 40° C. and filtered through Celite. The filtrate was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume) to afford the title compound as a pale yellow solid (1.8 g).

Workup

additionwas treated with bis[copper(I)triflate]benzene complex (3.3 g)
temperatureThe mixture was cooled to 40° C.
filtrationfiltered through Celite
additionThe filtrate was diluted with ethyl acetate
washwashed with saturated aqueous sodium hydrogen carbonate solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume)

Sources & evidence

ORD record: ord-e6860fa3dd284e538828c0fd6b82207e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

Loading…