Hydrochloric Acid → {2-[3-(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-ureido]-ethyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylamine (233 mg, 1.28 mmol) and pyridine (310 μL, 3.53 mmol) in tetrahydrofuran (6 mL) at 25° C. was treated with a solution of triphosgene (190 mg, 0.64 mmol) in tetrahydrofuran (2 mL) followed by (2-tert-butoxycarbonylamino-ethyl)-carbamic acid (225 mg, 1.40 mmol). The reaction was stirred at 25° C. overnight. At this time, the reaction was treated with a 1N aqueous hydrochloric acid solution and was stirred at 25° C. for an additional 30 min. At this time, the resulting precipitate was collected by filtration and was washed with a 1N aqueous hydrochloric acid solution and diethyl ether to afford {2-[3-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-ureido]-ethyl}-carbamic acid tert-butyl ester (170 mg, 36.8%) as a pink solid; LRMS for C14H20N6O4S (M+H)+ at m/z=369.

Provenance & Evidence