2-Methyl-2-thiopseudourea sulfate → 2-(Methylthio)-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine

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Reaction Steps

To a solution of 4.83 g (12.63 mmol) of 4-[(dimethylamino)methylene]-1-tritylpyrrolidin-3-one in anhydrous ethanol (50 mL) was added sodium ethoxide (11.8 mL, 21% in ethanol). After stirring for 5 min, 3.51 g (25.25 mmol) of 2-methyl-2-thiopseudourea sulfate was aided and the reaction mixture heated at reflux temperature for 1 h. The mixture was cooled to ambient temperature and 3.51 g (25.25 mmol) of 2-methyl-2-thiopseudourea sulfate was added followed by 11.8 mL (21% in ethanol) of sodium ethoxide. The reaction mixture was refluxed for 1 h and cooled to ambient temperature. This process was repeated two additional times at which point the reaction mixture was evaporated in vacuo, diluted with 200 mL of a 1:1 mixture of ethyl acetate and saturated aqueous brine. The layers were separated and the aqueous phase extracted with three 100-mL portions of ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was chromatographed on a Biotage® system (silica gel, 0 to 25% ethyl acetate/hexanes gradient) to yield the title compound as a white solid. LC/MS=410.3 (M+1).

Provenance & Evidence