2-Amino-5-methylthiazole → HCID 57504746, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminium (1M in heptane) (3.97 mL, 3.97 mmol) was added to 5-methylthiazol-2-amine (0.434 g, 3.80 mmol) in DCM (40 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes. (S)-Methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-hydroxypropanoate (Intermediate AD3) (1 g, 3.45 mmol) in DCM (10 mL) was added and the reaction was allowed to warm to room temperature and then heated at reflux for 2 hours, then left to cool to room temperature overnight. Rochelle solution (20%; 50 mL) was added and the resulting mixture was stirred vigorously for 90 mins. The mixture was diluted with DCM (50 mL) and the layers separated. The organics were dried (MgSO4) and evaporated (733 mg). The residue was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in EtOAc to afford the product (0.300 g, 23.37%).

Provenance & Evidence