Dichloromethane methanol → [6-(4-Amino-phenoxy)-pyrimidin-4-yl]-(4-methoxy-phenyl)-amine

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Reaction Steps

(4-Methoxy-phenyl)-[6-(4-nitro-phenoxy)-pyrimidin-4-yl]-amine (Stage 47.2; 1.06 g, 3.13 mmol) dissolved in THF/EtOH (1:2; 27 mL) is hydrogenated in the presence of Raney-Ni (0.2 g) during 36 h. After filtering off the catalyst and washing with EtOH (20 mL), the solvent is evaporated under reduced pressure and flash chromatographed (silica gel, 4.5×26 cm, MeOH/CH2Cl2=5:95) giving a white solid: M+H=309.1; 1H-NMR (400 MHz, DMSO-d6): 9.23 (s, 1H, NH-pyrimidinyl), 8.22 (s, 1H, pyrimidine), 7.40/6.85/6.79/6.57 (d/d/d/d, 9.0 Hz, 8H, phenyl-oxo/phenyl-OMe), 5.81 (s, 1H, pyrimidinyl), 5.07 (s, 2H, NH2), 3.72 (s, 3H, CH3—O); Rf (MeOH/CH2Cl2=1:9): 0.44; HPLC (System 1): 3.45 min.

Provenance & Evidence