Reaction #7478

Reaction equation

water

3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

cesium carbonate

2-iodopropane

→

3-(β-D-glucopyranosyloxy)-5-methyl-1-isopropyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.DISTILLATIONthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
2. 2
   OtherThe obtained crude product
3. 3
   Otherwas purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=7/1)

Procedure

To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (56 mg) and cesium carbonate (23 mg) in N,N-dimethylformamide (1.5 mL) was added 2-iodopropane (0.043 mL) at 80° C., and the mixture was stirred for 35 minutes. To the reaction mixture was added water, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol). The obtained crude product was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=7/1) to give 3-(β-D-glucopyranosyloxy)-5-methyl-1-isopropyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole )45 mg).

Source