Phosphorus oxychloride → 4-Chloro-5-phenyl-2-pyridin-2-ylpyrimidine

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Reaction Steps

5-Phenyl-2-pyridin-2-ylpyrimidin-4-ol (4-1; 206 mg, 0.826 mmol) was stirred in 4 ml of anhydrous MeCN. Phosphorous oxychloride (0.077 ml, 0.83 mmol) was added and the resulting mixture was heated to reflux. After 1 h the reaction was cooled and concentrated in vacuo and quenched with half-saturated aqueous NaHCO3. The mixture was extracted 3× with DCM. The combined organic phases was dried over Na2SO4, filtered and concentrated to provide 4-chloro-5-phenyl-2-pyridin-2-ylpyrimidine (4-2). 1H NMR (CDCl3): δ 8.88 (s, 1H), 8.84 (s, 1H), 8.57 (d, J=8.0 Hz, 1H), 7.90 (dt, J=1.5, 7.6 Hz, 1H), 7.53 (m, 5H), 7.46 (dd, J=4.9, 7.1 Hz, 1H).

Provenance & Evidence