2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-5-methoxy[1,3]thiazolo[5,4-b]pyridine

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Reaction Conditions

Reaction Steps

3-Amino-6-methoxy-2-pyridinethiol (0.8 g, Maybridge Co.) and 2-chloro-1,1,1-triethoxyethane (1.26 g) were combined in ethanol (5 mL) and heated at 90° C. in a sealed tube for 2 hours. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (2:1, dichloromethane:hexanes) to provide the title compound. 1H NMR (CDCl3, 300 MHz) δ 4.00 (3H, s), 4.88 (2H, s), 6.88 (1H, d, J=8.7 Hz), 8.10 (1H, d, J=8.7 Hz); MS (DCI/NH3) m/z 215.0 (M+H)+.

Provenance & Evidence