Methyl iodide → HCID 21106341, compound

Participants

Reaction Conditions

Reaction Steps

A solution 6-iodo-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine VI (2.68 g, 8.24 mmol) in tetrahydrofuran (100 mL) was treated with powdered sodium hydroxide (0.66 g, 16.5 mmol), iodomethane (0.62 mL, 9.96 mmol), and tetrabutylammonium bromide (0.8 g, 2.48 mmol) and the resulting mixture stirred at 25° C. for 18 h. The resulting mixture was concentrated in vacuo. The residue was partitioned between methylene chloride (70 mL) and water (70 mL) and this mixture was stirred at 25° C. for 30 min. The precipitate was isolated by filtration, washed with water, and dried in vacuo to afford 6-iodo-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (2.67 g, 95.5%) as a yellow solid; 1H NMR (DMSO-d6, 300 MHz) δ 7.58 (s, 1H), 7.47 (d, J=2.93 Hz, 1H), 6.99 (d, J=2.93 Hz, 1H), 6.78 (broad s, 2H), 5.83 (broad s, 2H), 4.16 (s, 3H).

Provenance & Evidence