Methylamine → Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

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Reaction Steps

To a solution of 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (42 g, 0.181 mol) in EtOH (400 mL) was added MeNH2 (12.3 g, 0.398 mmol) in EtOH (100 mL) at 0° C. and the mixture stirred for 3 h. The mixture was concentrated to remove most of the solvent and then partitioned between H2O (200 mL) and CH2Cl2 (500 mL). The organic layer was washed with brine, dried and concentrated to give 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester as a white solid (36.0 g, 88% yield). 1H NMR (300 MHz, CDCl3): δ 8.59 (s, 1H), 8.18 (brs, 1H), 4.31 (q, J=7.2 Hz, 2H), 3.05 (d, J=4.8 Hz, 3H), 2.52 (s, 3H), 1.34 (t, J=7.2 Hz, 3H).

Provenance & Evidence