Hydrogen Bromide → 2-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

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Reaction Steps

To a stirred suspension of 1.00 g (5.37 mmol) 2,2-dicyano-1-methylsulfanyl-vinyl-cyanamide sodium salt in 10 ml acetic acid at 5° C. was added dropwise 10 ml hydrobromic acid solution (33% in acetic acid) and the mixture was stirred at room temperature for 30 minutes. The mixture was then poured onto 100 ml ice-water added. The resulting crystals were collected by filtration and washed with water (ca 500 ml) until the washings were free of bromide ion. Chromatography (ethyl acetate/hexane 1/4) afforded 1.09 g (83%) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 246 (M{81Br}+, 93), 244 (M{79Br}+, 94), 165 ([M—Br]+, 100).

Provenance & Evidence