Acetic Acid → 4-(6-Chloropyrimidin-4-yl)-3-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-chloro-6-(2-methoxy-4-nitrophenyl)pyrimidine (0.6 g, 2.259 mmol) in EtOH (Ratio: 2.000, Volume: 10 mL) was stirred at 80° C. to make most of the material solublized, Acetic Acid 20% (Ratio: 1.000, Volume: 5 mL) and iron powder (0.883 g, 15.81 mmol) were added. The resulting mixture was refluxed for 1 h. The reaction was concentrated under vacuum. The residue was partitioned between EtOAc/1.0 M aqueous NaOH. The aqueous layer was extracted with EtOAc (3×20 ml). The combined organic layers were washed with aqueous sodium bicarbonate (2×20 ml) and brine (20 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage Horizon system (25 g column of Thomson Single Step, EtOAc/Hexane, Griadient: 0%˜80%). Desired fractions were collected, concentrated and the residue was triturated with DCM to get 0.5 g (82%) of product as light-yellow solid. LC-MS (M+H)+=236. 1H NMR (400 MHz, CDCl3) δ ppm 3.91 (s, 3H) 4.07 (br. s., 2H, NH2) 6.27 (d, J=2.26 Hz, 1H) 6.40 (dd, J=8.53, 2.26 Hz, 1H) 8.04 (d, J=1.25 Hz, 1H) 8.07 (d, J=8.28 Hz, 1H) 8.91 (d, J=1.25 Hz, 1H).

Provenance & Evidence