Dimethylformamide → HCID 131717067, compound

Participants

Reaction Steps

To a solution of 103 mg (0.15 mmol) 2-butyl-4-amino-5-carbomethoxy-1-(2'-(N-triphenylmethyltetra-zol-5-yl)-biphen-4-yl)methylimidazole (Example 1, Step I) in 1 mL dry DMF at room temperature was added 7 mg sodium hydride/oil dispersion (60% dispersion; 0.18 mmol, 1.1 eq). After 15 minutes at room temperature, two drops of methyl iodide were added and the mixture capped tightly and stirred at room temperature for 16 hours. Two drops of glacial acetic acid were added and the mixture diluted into 20 mL ethyl acetate and washed with pH 7.0 phosphate buffer (2×) and brine (1×). The organic layer was removed, dried over magnesium sulfate, filtered and stripped; the residue was purified by medium pressure liquid chromatography on silica, eluting with ethyl acetate/hexane (2:1) to afford 65 mg of a 2:1 mixture of mono- and di-methylated products in addition to 23 mg of recovered starting material.

Provenance & Evidence