(4-Aminophenoxy)benzene → 4-[4-(4-Phenoxy-phenylamino)-quinazolin-6-ylethynyl]-tetrahydro-pyran4-ol hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-Chloro-quinazolin-6-ylethynyl)-tetrahydro-pyran-4-ol (43 mg, 0.15 mmol) and 4-phenoxyaniline (28 mg, 0.15 mmol) in 2 mL of t-BuOH/1,2-dichloroethane (1:1) was heated at 90° C. with stirring in a reaction vial for 1 hour. The reaction was cooled, diluted with CH2Cl2 and the product was collected by filtration to provide 52 mg (73%) of 32 as a yellow solid: 1H NMR (CD3OD) δ 1.86 (m, 2H), 2.02 (m, 2H), 3.74 (m, 2H), 3.92 (m, 2H), 7.05 (m, 4H), 7.15 (t, J=7.6 Hz, 1H), 7.38 (t, J=7.6 Hz, 2H), 7.69 (d, J=6.8Hz, 2H), 7.81 (d, J=7.2Hz, 1H), 8.07 (d, J=7.2 Hz, 1H), 8.75 (s, 2H); HPLC: 6.36 min.

Provenance & Evidence