Triethylamine → HCID 59242070, compound

Participants

Reaction Steps

To a suspension of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.132 g (0.5 mmol) with Et3N 0.2 mL in CH2Cl2 10 mL was added methylsulfonyl chloride 0.115 g (1.0 mmol) at 23° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 30 mL, washed with water, sat. Na2CO3 aqueous solution and dried on anhydrous MgSO4. After removal of solvents, the crude product was subjected to gradient column chromatography (EtOAc/hexanes, 0% to 100%), but the compound was only obtained in <80% purity. Therefore, the crude compound was purified with preparative HPLC to give the titled compound in 15% yield. 1H NMR (CD3OD, 400 MHz): δ 7.86-7.82 (m, 1H), 7.72-7.67 (m, 1H), 7.44-7.42 (m, 4H), 7.29-7.24 (m, 1H), 6.94 (d, 1H, J=8.6 Hz), 3.84 (s, 3H), 3.07 (s, 3H), 2.78 (s, 3H). m/e: 343.1339 (M+1).

Provenance & Evidence