HRID1785174

反应详情

EQUATION

反应方程式

HRID 1785174 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added over 5 min. to a stirred mixture of 5-chloro-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl-amine (0.190 g) and 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.230 g) in DMF (6.5 ml) cooled to 0° C. under a nitrogen atmosphere; the resultant mixture was stirred for 1 hr at ambient temperature. The reaction mixture was diluted with saturated aqueous ammonium chloride (70 ml) and extracted with ethyl acetate (3×25 ml). The organic extracts were washed with brine (25 ml), dried over sodium sulphate and then evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methanol in dichloromethane as eluent. There was thus obtained the title compound as a racemate and in the form of a solid (0.314 g). NMR Spectrum: (DMSOd6) 1.42 (d, 3H), 1.95 (m, 2H), 2.37 (m, 4H), 2.45 (t, 2H), 3.35 (s, 3H), 3.57 (m, 4H), 3.92 (s, 3H), 4.18 (t, 2H), 4.39 (q, 1H), 6.15 (s, 2H), 7.13 (s, 1H), 7.18 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.50 (s, 1H); Mass Spectrum: M+H+ 555 and 557.

WORKUP

后处理

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. washThe organic extracts were washed with brine (25 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methanol in dichloromethane as eluent