2-Amino-4-methylthiazole → HCID 25208982, compound

Participants

Reaction Steps

To a solution of 3.72 g (32.6 mmol) of 2-Amino-4-methylthiazole in 40 ml of dry dioxane were added dropwise 15.9 ml (31.8 mmol, 4.0 equiv.) of a 2M solution of trimethylaluminium in hexane. The solution was stirred for 30 min at room temperature. Then a solution of 1.94 g (7.95 mmol) of 4-Bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester in 6 ml of dry dioxane was added dropwise and the reaction was heated to 100° C. for 1.5 h. The reaction was quenched by cautious addition of 2.5 ml of water. Then approximately 10 g of anhydrous sodium sulfate were added to bind the water and the mixture was stirred vigorously for 5 min. The mixture was diluted by addition of 20 ml of methylene chloride and filtered over Speedex filteraid which was washed with methylene chloride. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (heptane/ethyl acetate 4:1) to yield the title compound (1.95 g, 79%) as a yellow solid, MS (ISP): m/e=312.0, 314.0 (M+H)+.

Provenance & Evidence