1092539-44-0

42841-64-5

1092523-24-4

1092538-80-1

3 g (10.69 mmol) of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro[1,8]diazanaphthalene-3-carboxamide was suspended in 20 mL of methanol in an 80 mL microwave tube. A DMF/Et3N mixture (V/V; 1/1) was added to the suspension followed by argon bubbling for 10 min. 1.83 g (±)-1-methoxy-2-methyl-3-butyn-2-ol (16.03 mmol), 0.081 g CuI (0.43 mmol), and 0.375 g bis(triphenylphosphine)palladium(II) dichloride (0.53 mmol) were added sequentially. The sealed tube was placed in a microwave reactor (CEM Discover model) and heated at 90 °C for 60 min at 100 W power. After completion of the reaction, the mixture was cooled and evaporated to dryness. The residue was dissolved in mixed ethyl acetate/THF solvent and washed with 0.1 N HCl aqueous solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography (dry sample, elution gradient: cyclohexane/ethyl acetate, 30:70 to 20:80) to give 2.49 g of light yellow solid product. The product can be recrystallized from ethanol to give white crystals with a melting point of 211 °C. Mass spectrum (MH+): 358. yield: 65%.1H NMR (DMSO-d6, 400 MHz, δ ppm): δ 11.75 (s, <1H, broad peak); 11.00 (q, 1H, broad peak); 8.45 (d, 1H); 8.00 (s, 1H, broad peak); 7.4 (d, 1H); 5.8 (s, 1H); 4.4 (q, 2H); 3.5 (q, 2H). 2H); 3.5-3.3 (m + s, 5H); 2.8 (d, 3H); 1.45 (s, 3H); 1.2 (t, 3H).