Aniline → HCID 178433114, compound

Participants

Reaction Steps

To a 5-mL, wheaton vial were added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (100 mg, 0.41 mmol) and aniline (Aldrich Chemical Company) (0.37 mL, 4.1 mmol), followed by EtOH (1.5 mL). The reaction was heated at reflux for 4 h. The reaction mixture was allowed to cool to room temperature and the precipitate was collected by filtration, washed with hexanes, dried in a vacuum oven overnight to give 114 mg of a brown solid. The material was recrystallized from EtOH to give 57 mg (41%) of the title compound as an off-white solid. 1H NMR (DMSO-d6; 400 MHz): d 2.67 (s, 3), 7.04 (s, 1), 7.21-7.23 (m, 1), 7.44-7.59 (m, 5), 8.03 (d, 2, J=8.0), 8.15 (d, 2, J=8.0), 11.61 (br s, 1), 13.84 (br s, 1). MS m/z: 301 (M+1).

Provenance & Evidence