Acetonitrile → N-tert-Butyl-7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-amine

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Reaction Conditions

Reaction Steps

A mixture of 5-Amino-4,6-dichloropyrimidine (9.0 g, 55 mmol), tert-butylisothiocyanate (7.02 g, 61.0 mmol), Cesium Carbonate (39.7 g, 122 mmol) and acetonitrile (200 mL) was stirred at 50° C. for 16 hours. The mixture was allowed to cool to rt. To the mixture, were added water and EtOAc. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (6.45 g, 48%) as a white solid. LCMS: (AA) ES+ 243, 245. 1H NMR (400 MHz, d6-DMSO) δ: 8.71 (bs, 1H), 8.49 (s, 1H), 1.45 (s, 9H).

Provenance & Evidence