反应 #2204937

反应方程式

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2-methoxymethylimidazole

phenylguanidine hydrogen carbonate

sodium methoxide

→

title compound

2-Anilino-4-(1-isopropyl-2-methoxymethylimidazol-5-yl)pyrimidine

溶剂

DMA

反应条件

后处理

1. 1
   其他The volatiles were evaporated in vacuo the residues
2. 2
   萃取The solution was extracted DCM (3×50 ml)
3. 3
   洗涤The combined extracts were washed with water (50 ml)
4. 4
   干燥brine (50 ml), dried
5. 5
   其他the volatiles removed by evaporation
6. 6
   其他The residue was purified by flash silica chromatography
7. 7
   洗涤eluting with DCM:MeOH (100:0 increasing in polarity to 97:3)

实验过程

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2-methoxymethylimidazole (Method 50; 1.26 g, 5 mmol), phenylguanidine hydrogen carbonate (1.09 g, 5.5 mmol) and sodium methoxide (594 mg, 11 mmol) were suspended in anhydrous DMA (10 ml) and the mixture heated at 110° C. for 3 hours. The volatiles were evaporated in vacuo the residues was suspended in water (50 ml). The solution was extracted DCM (3×50 ml). The combined extracts were washed with water (50 ml) and then brine (50 ml), dried and the volatiles removed by evaporation. The residue was purified by flash silica chromatography eluting with DCM:MeOH (100:0 increasing in polarity to 97:3) to give the title compound as brown oil. NMR: 1.43 (d, 6H), 3.30 (s, 3H), 4.56 (s, 2H), 5.54 (m, 1H), 6.96 (t, 1H), 7.05 (d, 1H), 7.24 (t,2H), 7.44 (s, 1H), 7.65 (d, 2H), 8.41 (d, 1H), 9.42 (s, 1H); m/z 324.

来源