Methylamine → 2-chloro-N-methyl-5-nitropyrimidin-4-amine

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Reaction Steps

A solution of 5.82 g (30 mmol) of 2,4-dichloro-5-nitropyrimidine (N. Whittaker, J. Chem. Soc., 1951;1565–1570) in 100 mL of tetrahydrofuran (THF) is cooled to −78° C. and a solution of 4.66 g (60 mmol) of 40% aqueous methylamine in 20 mL of 2-propanol is added dropwise over 5 minutes. After a further 10 minutes at −78° C., the mixture is allowed to warm to room temperature, and the solvent is removed under vacuum. The residue is then extracted into ethyl acetate (EtOAc), washed with water, and dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with hexane/EtOAc (92:8), gives 4.87 g (86%) of the title compound: mp (hexane) 86–87° C. (lit. mp: 90–91° C.; G. B. Barlin, J. Chem. Soc. (B), 1967:954–958).

Provenance & Evidence