2-methylsulfanyl-5-nitropyrimidine → 5-Pyrimidinamine, 2-(methylthio)- (9CI)

Participants

Reaction Conditions

Reaction Steps

A solution of 5 g (29.2 mmol) of 2-methylsulfanyl-5-nitropyrimidine in 200 mL of absolute ethanol and 120 mL of glacial acetic acid was added 16.31 g (292 mmol) of iron powder and the mixture was heated in an oil bath maintained at 80° C. for 2 hours. The reaction was diluted with 250 mL of ethyl acetate and filtered through CELITE® filter aid. The filtrate was washed with two portions of 100 mL of water, and the pH of the organic layer was adjusted by adding saturated aqueous sodium carbonate solution until the pH was 8. The organic layer washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 2.1 g (51%) of 2-methylsulfanylpyrimidin-5-ylamine.

Provenance & Evidence