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

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)+.

1. temperaturethe reaction was heated to 100° C. for 1.5 h
2. customThe reaction was quenched by cautious addition of 2.5 ml of water
3. additionThen approximately 10 g of anhydrous sodium sulfate were added to bind the water
4. stirringthe mixture was stirred vigorously for 5 min
5. additionThe mixture was diluted by addition of 20 ml of methylene chloride
6. filtrationfiltered over Speedex filteraid which
7. washwas washed with methylene chloride
8. concentrationThe filtrate was concentrated in vaccuo
9. customthe residue was purified by flash chromatography (heptane/ethyl acetate 4:1)

ORD record

ord-81396825b7324ad0b53af73bf0bdc407

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951824B2