[4-(6-Chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester → [4-(5-Amino-6-chloro-pyrimidin-4-ylamino)-phenyl]acetic acid ethyl ester

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Reaction Steps

A mixture of [4-(6-chloro-5-nitro-pyrimidin-4-ylamino)-phenyl]-acetic acid ethyl ester (0.400 g, 1.19 mmol) and Raney Ni (˜0.100 g) in THF (10 mL) is stirred for 20.5 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. Purification of the residue by silica gel column chromatography (Hexane/EtOAc, 70:30) provides the title compound as a yellow solid: ES-MS: 307.1 [M+H]+; single peak at tR=3.81 min (System 1); Rf=0.06 (Hexane/EtOAc, 70:30).

Provenance & Evidence