Hydrochloric Acid → HCID 69310879, compound

Participants

Reaction Conditions

Reaction Steps

Chlorosulphonic acid (250 μl, 3.6 mmol) was added dropwise to solution of 2-anilino-4-(1-ethylimidazol-5-yl)pyrimidine (Method 32; 250 mg, 0.9 mmol) in thionyl chloride (5 ml) cooled at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of cyclopropylamine (1 ml, 13.5 mmol) in MeOH (4ml) added. The mixture was stirred for 15 minutes and the volatiles were evaporated in vacuo. Water (20ml) was added and the resultant solid was washed with water (2×10 ml), ether (2×10 ml) and dried under vacuum at 60° C. for 18 hr. The resultant solid was dissolved in MeOH (4 ml) and treated with 1M HCl in ether (0.62 ml, 0.62 mmol). The solvent was evaporated in vacuo and the resultant solid triturated with ether, collected by filtration and dried under vacuum at 60° C. to yield the title compound (220 mg, 56%) as a golden solid. NMR: 0.34 (m, 2H), 0.52 (m, 2H), 1.52 (t, 3H), 2.21 (m, 1H), 4.77 (q, 2H), 7.43 (d, 1H), 7.74 (m, 3H), 7.93 (d, 2H), 8.54 (s, 1H), 8.72 (d, 1H), 9.41 (s, 1H), 10.20 (brs, 1H); m/z 385.

Provenance & Evidence