Diisopropylamine → N-[5-chloro-7-(phenylethynyl)-1,3-benzodioxol-4-yl]-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

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Reaction Steps

A mixture of N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.17 g, 0.285 mmol), phenyl acetylene (0.07 ml, 0.63 mmol) and diisopropylamine (0.088 ml, 0.63 mmol) in ethyl acetate (4 ml) was cooled to −20 C under a nitrogen atmosphere. To this was added copper (I) iodide (0.016 g, 0.085 mmol) and bis(triphenylphospine)palladium (II) chloride (0.04 g, 0.057 mmol). The mixture was allowed to warm to ambient temperature and then stirred overnight. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 0-10% methanol in dichloromethane gave the product as a solid (0.108 g, 66%). NMR Spectrum: (DMSOd6 at 373k+d4 acetic acid) 2.10 (m, 2H), 2.76 (t, 4H), 2.83 (t, 2H), 3.69 (t, 4H), 3.97 (s, 3H), 4.24 (t, 2H), 6.12 (s, 2H), 7.15 (s, 1H), 7.30 (s(broad), 1H), 7.42 (m, 3H), 7.54 (m, 2H), 7.95 (s, 1H), 8.63 (s(broad), 1H). Mass Spectrum: M+H+ 573 and M+H− 571.

Provenance & Evidence