Hydrochloric Acid → Aminocyclopyrachlor-methyl

Participants

Reaction Steps

Sodium methoxide in methanol (25%, 3 drops) was added to ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate (i.e. the product of Example 7) (0.53 g) in methanol (15 mL). The mixture was boiled for 1 h. The mixture was allowed to cool to room temperature, and was partitioned between hydrochloric acid (0.28 g, 1.16 mmol) in methanol (5 mL). The mixture was boiled for 90 minutes. The mixture was allowed to cool to room temperature, and ammonium chloride (0.3 g, 5.6 mmol) was added. After 10 minutes the solvent was removed under reduced pressure. The mixture was extracted with ethyl acetate (50 mL), and the extracts evaporated to give the product as a white solid (0.24 g, 92% yield). Product recrystallized from ethyl acetate melted at 148.5-149.5° C.

Provenance & Evidence