Dimethyl Sulfate → 1-Methyl-2-isopropylamino-5-methoxycarbonylpyrimidinium hydroxide

Participants

Reaction Steps

A mixture of 27.45 g (0.140 mol) of 2-isopropylamino-5-methoxycarbonylpyrimidine and 56 ml (2 eq; 0.59 mol) of dimethyl sulfate in 440 ml of anhydrous tetrahydrofuran is refluxed for 24 hours. The reaction medium is extracted with ethyl acetate and water. Purification on silica gel (eluent: 95 CH2Cl2 [sic]/5% MeOH/saturation with gaseous NH3) of the oil resulting from the evaporation of the aqueous phases gives 37.2 g of 1-methyl-2-isopropylamino-5-methoxycarbonylpyrimidinium hydroxide (yield: 82%).

Provenance & Evidence