P-Anisidine → (2-Chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine

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Reaction Steps

2.46 g (19.0 mmol) Diisopropylethylamine are added slowly to a solution of 3.36 g (17.3 mmol) 2,4-dichloro-5-nitropyrimidine and 2.13 g (17.3 mmol) p-anisidine in 30 ml dioxane. The mixture is stirred for 3 hours at room temperature. Then it is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with ethyl acetate/cyclohexane as eluent giving (2-chloro-5-nitro-pyrimidin-4-yl)-(4-methoxy-phenyl)-amine as orange crystals; HPLC/MS (B): 2.24 min, [M+H] 281;

Provenance & Evidence