反应详情

To a cooled (ice/water), stirred solution of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-iodoaniline (1.34 g, 2.78 mmol) and diethylisopropylamine (0.7 mL, 4.0 mmol) in MTHF (5 mL) was added 4,6-dichloroprimidine-5-carbonyl chloride (560 mg, 2.65 mmol). After 5 minutes, the cooling bath was removed and the slurry was stirred for 5 hours. Aqueous hydrochloric acid (1N, 5 mL) was added and the mixture was allowed to stand for 72 hours. The layers were separated and the aqueous layer was washed with MTHF (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo to afford an oil. Chromatography (40 g silica gel column, 20-100% EtOAc:heptane) afforded the title compound, 542 mg. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.62 (d, 2H), 7.17 (d, 2H), 4.07 (t, 2H), 3.91 (q, 2H). m/z=438.0 (M+1).

1. customthe cooling bath was removed
2. additionAqueous hydrochloric acid (1N, 5 mL) was added
3. waitto stand for 72 hours
4. customThe layers were separated
5. washthe aqueous layer was washed with MTHF (2×)
6. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customto afford an oil