4-Aminopyrimidine → 4-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A flask was charged with perfluorophenyl 4-(4-chloro-2-methoxyphenyl)quinazoline-7-sulfonate (Intermediate AAAAAA; 1.0 g, 1.935 mmol), pyrimidin-4-amine (0.193 g, 2.032 mmol), and THF (19.35 ml) and cooled to 0° C. LHMDS (1.0M in THF) (4.06 ml, 4.06 mmol) was added drop wise and the reaction was stirred for 30 minutes. The reaction was quenched with saturated ammonium chloride solution, diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-10% MeOH:DCM) to afford 4-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ=13.28 (br. s., 1H), 9.46 (s, 1H), 8.57 (t, J=1.0 Hz, 1H), 8.48 (d, J=1.7 Hz, 1H), 8.22 (d, J=6.5 Hz, 1H), 8.03 (dd, J=1.9, 8.8 Hz, 1H), 7.83 (d, J=8.7 Hz, 3H), 7.47 (d, J=8.1 Hz, 1H), 7.38 (d, J=1.9 Hz, 1H), 7.25 (dd, J=2.0, 8.1 Hz, 1H), 7.00 (d, J=6.7 Hz, 1H), 3.72 (s, 3H). m/z (ESI) 428.2 (M+H)+.

Provenance & Evidence