تفاعل #2204937

معادلة التفاعل

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

المذيبات

DMA

ظروف التفاعل

المعالجة

1. 1
   أخرىThe volatiles were evaporated in vacuo the residues
2. 2
   استخلاصThe solution was extracted DCM (3×50 ml)
3. 3
   غسيلThe combined extracts were washed with water (50 ml)
4. 4
   تجفيفbrine (50 ml), dried
5. 5
   أخرىthe volatiles removed by evaporation
6. 6
   أخرىThe residue was purified by flash silica chromatography
7. 7
   غسيلeluting with DCM:MeOH (100:0 increasing in polarity to 97:3)

الإجراء التجريبي

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.

المصدر