Dimethylformamide → HCID 89782069, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylcyclopropanamine hydrochloride (Small Molecules Inc.; 0.32 g, 2.96 mmol), DIEA (1.37 mL, 7.89 mmol) and 8-bromo-2-chloroquinazoline (0.48 g, 1.97 mmol) in 5 mL of dioxane was heated in a microwave at 125° C. for 45 min. LCMS indicated the presence of starting material (8-bromo-2-chloroquinazoline). The reaction mixture was treated with 2 mL of DMF and heated in a microwave at 130° C. for 35 min. It was diluted with 50 mL of EtOAc, washed with 5 mL of water followed by 5 mL of brine. The organic layer was concentrated and the residue was stirred in 2 mL of ether and 10 mL of hexanes. The solid was filtered and dried to give 8-bromo-N-(1-methylcyclopropyl)quinazolin-2-amine (499a; 0.51 g, 1.83 mmol, 93% yield) in about 80% purity. This material was used in next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.12 (1H, br.), 8.05 (1H, dd, J=7.6, 1.2 Hz), 7.95 (1H, s), 7.83 (1H, d, J=7.4 Hz), 7.16 (1H, t, J=7.7 Hz), 1.51 (3H, s), 0.78 (2H, m), 0.65 (2H, m). MS (ESI, pos. ion) m/z: 278.1/280.1 (M+1).

Provenance & Evidence