P-Anisidine → 2-Chloro-N-(4-methoxyphenyl)pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

Sodium bicarbonate (1.26 g, 11.9 mmol) is added to a slurry of 2,4-dichloropyrimidine (1.01 g, 6.78 mmol) in ethanol (30 mL) at 0° C. 4-Methoxyaniline (840 mg, 6.82 mmol) is added and the slurry stirred at 0° C. for 6 hours. The reaction mixture is warmed to room temperature for 1 hour, then diluted with water (50 mL) and extracted three times with CHCl3 (50 mL). The combined organic layers are washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give crude product which is purified over silica (10% Et2O/CH2Cl2) to afford 1.20 g (75% yield) of the desired product as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=5.8 Hz, 1H), 7.20 (d, J=9.0 Hz, 2H), 7.05 (br s, 1H), 6.94 (d, J=9.0 Hz, 2H), 6.41 (d, J=5.8 Hz, 1H), 3.83 (s, 3H); MS (ESI) m/z 236 (M+1).

Provenance & Evidence