Tetrahydrofuran → HCID 68881822, compound

Participants

Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (2.66 ml) in tetrahydrofuran (1.0M, 2.66 mmol) was added dropwise to an ice-cold solution of 4-chloro-7-(4-chlorobutoxy)-6-methoxyquinazoline (0.4 g, 1.33 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.35 g, 1.47 mmol) in dimethylformamide (4 ml). The mixture was allowed to warm to room temperature over 1 hour. A saturated solution of ammonium chloride was added and the mixture was partitioned between water and dichloromethane. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give 7-(4-chlorobutoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine as a gum (0.493 g, 73%). NMR Spectrum: (CDCl3) 2.05 (m, 4H), 3.48 (s, 3H), 3.65 (t, 2H), 3.98 (s, 3H), 4.23 (t, 2H), 4.37 (s, 2H), 6.08 (s, 2H), 6.88 (s, 1H), 7.07 (s, 1H), 7.09 (s, 1H), 7.25 (s, 1H), 8.63 (s, 1H). Mass Spectrum: M+H+ 504 and M+H− 502.

Provenance & Evidence