Methanol → 3-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine

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Reaction Steps

A mixture of the product of Example 74A (0.20 g, 1.3 mmol), the product of Example 78A (0.29 g, 1.3 mmol), tetrabutylammonium iodide (0.24 g, 0.64 mmol) in DMF (1.5 mL) was warmed to 85° C. and stirred for 16 h. The mixture was cooled to ambient temperature and quenched with saturated aqueous NaHCO3 (5 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 10% MeOH in EtOAc then 9:1:0.1 CH2Cl2:MeOH:NH4OH) to provide the title compound (0.18 g, 0.84 mmol, 65% yield). MS (DCI/NH3) m/z 209 (M+H)+.

Provenance & Evidence