反应详情

Methyl-2-formylpyrimidine-5-carboxylate (200 mg, 1.205 mmol) and 3-amino-4-hydroxy-5-isopropylbenzonitrile (212 mg, 1.205 mmol) were dissolved in methanol (5 ml). The mixture was concentrated, and then the residue was dissolved in dichloromethane (5 ml). To the above solution was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (300.9 mg, 1.325 mmol) at room temperature. The solution was stirred at room temperature for 30 min, and then concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash chromatography (hexanes-ethyl acetate=4:1, then 1:1) to provide of the title compound (139 mg) as a yellow solid. Mass spectrum (ESI) 322.8 (M+1). 1H NMR (500 MHz, CDCl3) δ 9.55 (s, 2H), 8.13 (s, 1H), 7.66 (s, 1H), 4.09 (s, 3H), 3.65 (m, 1H), 1.50 (d, 6H, J=6.8 Hz).

1. concentrationThe mixture was concentrated
2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
3. concentrationconcentrated
4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
5. extractionThe aqueous layer was extracted with ethyl acetate (3×)
6. washThe combined organics were washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (hexanes-ethyl acetate=4:1