Dichloromethane → 5-Methyl-3-(tetrahydro-pyran-2-ylmethyl)-3H-thiazol-2-ylideneamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-methylthiazole (1.2 g, 10.5 mmol) and 2-(bromomethyl)tetrahydro-2H-pyran (Aldrich, 1.5 mL, 11.6 mmol) was warmed to 85° C. and allowed to stir for 18 hours. The mixture was cooled to ambient temperature and purified by flash column chromatography (SiO2, first 10% CH3OH:EtOAc then 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to afford the title compound (1.1 g, 5.2 mmol, 49% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.12-1.32 (m, 1H) 1.44-1.63 (m, 2H) 1.79-1.95 (m, 2H) 2.06 (d, J=12.89 Hz, 1H) 2.25 (d, J=1.36 Hz, 3H) 3.33-3.45 (m, 1H) 3.65-3.78 (m, 1H) 3.86-4.01 (m, 2H) 4.44 (dd, J=14.92, 2.03 Hz, 1H) 6.56-6.65 (m, 1H) 9.48 (s, 1H); MS (DCI/NH3) m/z 213 (M+H)+.

Provenance & Evidence