Furan, 2-(bromomethyl)tetrahydro- → 5-methyl-3-((tetrahydrofuran-2-yl)methyl)thiazol-2(3H)-imine

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A mixture of 2-amino-5-methylthiazole (1.0 g, 8.7 mmol) and 2-(bromomethyl)tetrahydrofuran (Maybridge, 1.1 mL, 10 mmol) was warmed to 85° C. and allowed to stir for 24 hours. The mixture was then cooled to ambient temperature and purified via column chromatography (SiO2, 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to afford the title compound (1.5 g, 7.5 mmol, 86% yield). 1H NMR (300 MHz, CD3OD) δ ppm 1.55-1.70 (m, 1H) 1.89-2.01 (m, 2H) 2.07-2.20 (m, 1H) 2.28 (d, J=1.36 Hz, 3H) 3.72-3.82 (m, 1H) 3.86-4.00 (m, 2H) 4.08-4.24 (m, 2H) 6.98-7.04 (m, 1H); MS (DCI/NH3) m/z 199 (M+H)+.

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