1-Butanol → 4-Anilino-5-bromo-2-[4-(carboxyethyl)anilino]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-anilino-5-bromo-2-chloropyrimidine (Method 15; 1.50 g, 5.3 mmol), 4-aminophenylacetic acid (0.76 g, 5.0 mmol) and concentrated hydrochloric acid (0.98 ml, 5.3 mmol) in n-butanol (20 ml) was heated at 100° C. for 18 hours. The solid which separated out on cooling was collected by filtration and washed with n-butanol (20 ml) and diethyl ether (20 ml). The solid was dissolved in THF (20 ml) and methanol (10 ml). 2M Sodium hydroxide (3.80 ml, 7.6 mmol) was added and the solution was stirred for 18 hours. Volatile material was removed by evaporation and the residue was partitioned between ether (20 ml) and water (20 ml). The aqueous phase was separated and acidified to pH 3 to give the product as a white solid (350 mg). NMR: 7.0 (d, 2H), 7.2 (m, 1H), 7.4 (m, 2H), 7.5 (d, 2H), 7.6 (d, 2H), 8.2 (s, 1H), 8.6 (s, 1H), 9.3 (s, 1H); MS (MH+); 399, 401.

Provenance & Evidence