反应详情

温度

85 °C

A solution of methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (1.00 g, 2.56 mmol) and HCl (1.0 M in water, 3.84 mL, 3.85 mmol) in dioxane (10 mL) was stirred at 85° C. for 1 hour. After the removal of the solvent in vacuo, water was added to the residue. The aqueous solution was neutralized by 1M NaOH and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. To the resulting crude product was added phosphorus oxychloride (1.4 mL) and the mixture was stirred at 85° C. for 3 hours. After the removal of the excess phosphorus oxychloride, the residue was dissolved with ethyl acetate. The organic layer was washed with water, sat.NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica-gel, (chloroform:methanol, 98/2) to give methyl [5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (28 mg, 3%) as brown oil.

1. customAfter the removal of the solvent in vacuo, water
2. additionwas added to the residue
3. extractionextracted with ethyl acetate
4. washThe extracts were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. additionTo the resulting crude product was added phosphorus oxychloride (1.4 mL)
9. customAfter the removal of the excess phosphorus oxychloride
10. dissolutionthe residue was dissolved with ethyl acetate
11. washThe organic layer was washed with water
12. dry with materialNaHCO3 and brine, dried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure
15. customThe crude product was purified by column chromatography on silica-gel, (chloroform:methanol, 98/2)