Hydrochloric Acid → HCID 57636036, compound

Participants

Reaction Conditions

Reaction Steps

[6-(3-Amino-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]amine [1.46 g, Example 2] in dimethylformamide (4 mL) is added to concentrated hydrochloric acid and crushed ice (8 mL), The mixture is cooled to 0° C., treated with dropwise sodium nitrite (0.32 g) in water (3 mL). After stirring at 0° C. for 15 minutes this mixture is treated with a solution of copper chloride (0.36 g) in a saturated solution of sulfur dioxide in acetic acid (15 mL) previously cooled to 0° C. The reaction mixture is allowed to reach room temperature over 30 minutes and poured into water. The resulting precipitate is filtered and air dried affording 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzenesulfonylchloride [0.4 g, Intermediate (10)]. 1H NMR [(CD3)2SO]: δ 8 (1H, s); 7.7-7.8 (1H, m); 7.5 (1H, m); 7.2 (1H, s); 7.1 (2H, d, J=7.0); 6.8 (2H, d, J=7.0); 6.6 (1H, s); 4 (3H, s); 3.85 (3H, s); 3.7-3.8 (2H, m); 2.8 (2H, t).

Provenance & Evidence