1-Butanol → HCID 22048115, compound

Participants

Reaction Conditions

Reaction Steps

4-Anilino-5-bromo-2-chloropyrimidine (Method 1, 2.0 g, 7.03 mmol) was dissolved in n-butanol (40 ml) and methanol (10 ml). 4-Aminobenzyl alcohol (778 mg, 6.33 mmol) and ethereal hydrogen chloride (1.0M; 6.33 ml, 6.33 mmol) were added and the solution was heated at 100° C. for 20 hours. Volatile material was removed by evaporation and the residue as dissolved in ethylene glycol (20 ml). The solution was heated at 100° C. for 6 hours and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 0-4% methanol solution in DCM containing 0.5% aqueous ammonia solution, to give the product as a white solid (550 mg, 19%). NMR: 3.40 (t, 2H), 3.50 (dt, 2H), 4.37 (s, 2H), 4.57 (t, 1H), 7.09 (d, 2H), 7.10 (s, 1H), 7.15 (t, 1H), 7.36 (dd, 2H), 7.54 (d, 2H), 7.60 (d, 2H), 8.09 (s, 1H), 8.54 (s, 1H), 9.29 (s, 1H); MS (MH+): 415.2, 417.2.

Provenance & Evidence