Potassium Carbonate → (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester

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A mixture of Piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide trifluoroacetate salt (1.56 g, 3.82 mmol), diisopropylethylamine (2.7 mL, 15.5 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 30 minutes. To the mixture was added potassium carbonate (0.8 g, 5.8 mmole) and Bromo-(3-chloro-phenyl)-acetic acid methyl ester (1.0 g, 3.8 mmol) and the resulting mixture was stirred at room temperature overnight. Filtration and concentration gave a solid which was dissolved in methanol and absorbed onto 2 g of silica gel. The silica gel was loaded onto an Isco 120 g column and eluted using 0→5% Methanol/methylene chloride to yield (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester as a white powder; LRMS for C20H21ClN6O4S (M+H)+ at m/z=477. The NMR spectrum obtained on the sample is compatible with its structure.

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