反应 #355767

反应方程式

sodium hydrogen carbonate

bromine

4(1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

→

title compound

收率 24.0%

4-(4Bromo-1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxvethyl)sulphamoyl]anilino}pyrimidine

收率 24.0%

溶剂

water

acetic acid

acetic acid

反应条件

后处理

1. 1
   温度to cool
2. 2
   萃取The aqueous solution was extracted with EtOAc
3. 3
   其他dried
4. 4
   其他the volatiles removed by evaporation
5. 5
   其他The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10)

实验过程

A 1M solution of bromine in acetic acid (8.49 ml, 8.49 mmol) was added to a solution of 4(1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Example 35 in WO 02/20512; 3.1g, 7.71mmol) in acetic acid (24 ml) heated at 70° C. under nitrogen. The mixture was stirred at 70° C. for 1 hour, allowed to cool, diluted with water and carefully neutralised with saturated aqueous sodium hydrogen carbonate solution. The aqueous solution was extracted with EtOAc, the extracts combined, dried and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10) to give the title compound (1 g, 24%). NMR: 2.38 (s, 3H), 2.87 (s, 2H), 2.51 (q, 2H), 3.16 (s, 3H), 3.52 (s, 3H), 7.49 (s, 1H), 7.70 (d, 2H), 7.88 (d, 2H), 8.82 (s, 1H).

来源