Tetrahydrofuran → N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxy-7-(2-morpholin-4-ylethoxy)quinazolin-4-amine

Participants

Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (1.63 ml) in tetrahydrofuran (1.0M, 1.63 mmol) was added dropwise to an ice-cold solution of 6-methoxy-7-(2-morpholin-4-ylethoxy)-4-(pentafluorophenoxy)quinazoline (0.35 g, 0.74 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.213 g, 0.89 mmol) in dimethylformamide (4 ml). The mixture was allowed to warm to room temperature over 3 hours. 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. Flash chromatography on silica eluting with a mixture of 2-11% methanol in dichloromethane gave the product as a solid (0.029 g, 8%). NMR Spectrum: (CDCl3) 2.63 (m, 4H), 2.92 (t, 2H), 3.48 (s, 3H), 3.72 (m, 4H), 4.00 (s, 3H), 4.32 (t, 2H), 4.37 (s, 2H), 6.07 (s, 2H), 7.02 (s(broad), 1H), 7.07 (s, 1H), 7.12 (s, 1H), 7.25 (s, 1H), 8.62 (s, 1H). Mass Spectrum: M+H+ 525 and 527.

Provenance & Evidence