反应 #1810840

反应方程式

4-Amino-N-methyl-benzenesulphonamide

cyanamide

1-benzyl-5-(3-dimethylaminoprop-2-en-1-oyl)-2-methylimidazole

sodium methoxide

→

title compound

收率 70.0%

4-(1-Benzyl-2-methylimidazol-5-yl)-2-[4-(N-methylsulphamoyl)anilino]pyrimidine

收率 70.0%

溶剂

dimethylacetamide

MeOH

hydrogen chloride

反应条件

后处理

1. 1
   workup.ADDITIONadded
2. 2
   workup.ADDITIONwas added
3. 3
   温度to cool
4. 4
   温度the mixture heated
5. 5
   温度to reflux for one hour
6. 6
   温度to cool
7. 7
   其他was partitioned between EtOAc and aqueous sodium hydrogen carbonate solution
8. 8
   其他The organic layer was separated
9. 9
   洗涤washed with brine
10. 10
    干燥dried (Na2SO4)
11. 11
    其他the volatiles removed by evaporation
12. 12
    其他The residue was purified by chromatography on silica eluting with DCM/7N methanolic ammonia (96:4)
13. 13
    其他The purified product was triturated with minimal hot EtOAc

实验过程

4-Amino-N-methyl-benzenesulphonamide (250 mg, 1.34 mmol) was dissolved in the minimum amount of MeOH and 1M ethereal hydrogen chloride (1.34 ml) added. The volatiles were removed by evaporation and cyanamide (68 mg, 1.62 mmol) was added followed by dimethylacetamide (0.5 ml) and the mixture heated at 100° C. for 45 minutes. The mixture was allowed to cool and 1-benzyl-5-(3-dimethylaminoprop-2-en-1-oyl)-2-methylimidazole (Method 50; 230 mg, 0.86 mmol) and sodium methoxide (150 mg, 2.78 mmol) were added and the mixture heated to reflux for one hour. The mixture allowed to cool and was partitioned between EtOAc and aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (Na2SO4) and the volatiles removed by evaporation. The residue was purified by chromatography on silica eluting with DCM/7N methanolic ammonia (96:4). The purified product was triturated with minimal hot EtOAc to give the title compound (260 mg, 70%) as a cream solid. NMR: 2.28 (s, 3H), 2.37 (d, 3H), 5.96 (s, 2H), 6.93 (d, 2H), 7.15-7.28 (m, 5H), 7.54 (d, 2H), 7.75-7.81 (m, 3H), 8.40 (d, 1H), 9.86 (s, 1H); m/z 435.

来源