反应详情

Aqueous 3M HCl (15-30 ml) was added to a stirred solution of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide (0.15 M) in CH3CN (50 ml) at room temperature until the reaction became slightly turbid. After 16 hours, the reaction was partitioned between dichloromethane (200 ml) and 1M HCl (200 ml). The layers were separated, and the aqueous layer was extracted with dichloromethane (3×200 ml). The aqueous layer was basified carefully with solid NaHCO3 to pH 7-8. A solid forms which can be filtered and dissolved in CH3CN (100 ml). The organic solution is washed with sat. aq. NaHCO3 (50 ml), brine (50 ml), dried with Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel. The column was eluted first with a 1:1 mixture of dichloromethane/methanol followed by a mixture of 5% TEA/10% water/85% methanol to elute the product. The proper fractions were condensed. The dark yellow glass was dried overnight in vacuo giving 4-{2-[(2-aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile in 89% yield.

1. customthe reaction was partitioned between dichloromethane (200 ml) and 1M HCl (200 ml)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane (3×200 ml)
4. filtrationA solid forms which can be filtered
5. dissolutiondissolved in CH3CN (100 ml)
6. washThe organic solution is washed with sat. aq. NaHCO3 (50 ml), brine (50 ml)
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by flash chromatography over silica gel
11. washThe column was eluted first with a 1:1 mixture of dichloromethane/methanol
12. additionfollowed by a mixture of 5% TEA/10% water/85% methanol
13. washto elute the product
14. customcondensed
15. customThe dark yellow glass was dried overnight in vacuo