Hydrochloric Acid → {5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester

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Reaction Steps

To a suspension of compound 14.2 (23.7 mmol) in 1,4-dioxane (100 mL) was added HCl (70 mL of a 4.0 M in 1,4-dioxane) at 0° C. The reaction was allowed to warm to room temperature, stirred for 2 hours and concentrated to dryness to give a tan solid. The crude solid was suspended in THF (200 mL) and cooled to 0° C. Triethylamine (33 mL) was added followed by phenyl chloroformate (26.1 mmol). The reaction mixture was allowed to slowly warm to room temperature and stirred for 2 hours. Volatiles were removed under reduced pressure at room temperature, water was added and the solid collected by vacuum filtration. The solid was washed with ethyl ether and dried under vacuum to give {5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester (compound 16.1) in 80% yield as a tan solid.

Provenance & Evidence