反应详情

温度

72 °C

2-Amino-3-bromo-5-methyl-pyridine (1.0 g, 5.35 mmol) was added to a solution of sodium hydride (60%, 321 mg, 8.0 mmol) in dry THF (20 mL) at r.t. under nitrogen. After 30 minutes, 1-benzyl-3,5-dichloro-2(1H)-pyrazinone (see Vekemans, et. al., J. Heterocyclic Chem., 20, (1983), 919-923) (1.36 g, 5.35 mmol) was added, and the reaction stirred at 72° C. for 4 h. The solution was concentrated in vacuo and the residue was dissolved in CH2Cl2. Organics were washed with H2O and brine, dried (MgSO4), and concentrated. Purification by silica gel (2:1:1 hexanes/EtOAc/CH2Cl2) gave 860 mg (40%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.51 (s, 1H), 8.27 (s, 1H), 8.00 (s, 1H), 7.43 (s, 1H), 7.29-7.39 (m, 5H), 5.07 (s, 2H), 2.29 (s, 3H). MS (ES) [m+H] calc'd for C17H14BrClN4O, 405, 407; found 405, 407.

1. concentrationThe solution was concentrated in vacuo
2. dissolutionthe residue was dissolved in CH2Cl2
3. washOrganics were washed with H2O and brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customPurification by silica gel (2:1:1 hexanes/EtOAc/CH2Cl2)