Hydrochloric Acid → Mepanipyrim

Participants

Reaction Steps

Into a 50 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 1.30 g (0.005 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine and 10 ml of anhydrous tetrahydrofuran were charged and dissolved, and then the mixture was cooled to -10° under stirring in a nitrogen gas atmosphere. Then, 1.28 g (0.0114 mol) of potassium tert-butoxide was dissolved in 10 ml of anhydrous tetrahydrofuran and dropwise added thereto at a temperature of from -8° to -12° C., and the mixture was stirred at -15° C. for one hour. Then, 5 ml of 1N hydrochloric acid was dropwise added thereto, and 50 ml of water and a small amount of sodium hydrogen carbonate were added to bring the pH of the aqueous layer to 7. Then, the mixture was extracted with 70 ml of toluene, and the extract was dried over anhydrous sodium sulfate. The toluene layer was concentrated and subjected to silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 1.04 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 93.2%.

Provenance & Evidence