4,6-Dichloro-5-nitropyrimidine → [4-(6-Chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester

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Reaction Steps

4-Aminophenylacetic acid ethyl ester (0.93 g, 5.2 mmol) is added to a solution of 4,6-dichloro-5-nitropyrimidine (2 g, 10.4 mmol, 2 equiv). The resulting mixture is stirred for 2 h at rt and 4-aminophenylacetic acid ethyl ester (0.47 g, 2.6 mmol, 0.5 equiv) is added. The reaction mixture is stirred for 15 min and filtered. The filtrate is concentrated. The residue is dissolved in EtOAc and a saturated aqueous solution of sodium bicarbonate. The layers are separated. The aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (Hexane/EtOAc, 4:1) provides the title compound as a yellow solid: ES-MS: 335.0/337.0 [M-H]−; single peak at tR=4.73 min (System 1); Rf=0.22 (Hexane/EtOAc, 4:1).

Provenance & Evidence