Thionyl Chloride → (2-Chloro-6-methylpyrimidin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

5.00 g (28.97 mmol) of 2-chloro-6-methylpyrimidine-4-carboxylic acid and 5.17 g (118.97 mmol) of thionyl chloride are initially charged in 60 ml of dry toluene and stirred at 60° C. for 3 h. The reaction solution is concentrated on a rotary evaporator, 20 ml of toluene are added to the residue and the mixture is again concentrated to dryness on a rotary evaporator. The residue is dissolved in 40 ml of methyl tert-butyl ether and cooled to 5° C. At this temperature, a solution of 2.41 g (63.74 mmol) of sodium borohydride in 40 ml of water is added. After warming to RT, the reaction mixture is kept at 4° C. for 24 h. 40 ml of ethyl acetate and 10 ml of sat. sodium bicarbonate solution are then added to the mixture. The organic phase is washed twice with in each case 10 ml of water. After drying of the organic phase over magnesium sulphate, the solvent is removed on a rotary evaporator.

Provenance & Evidence