3-(二甲氨基)-2-甲基丙-2-烯醛

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 149.2 g (1.32 moles) of 2-methyl-3-dimethylaminoacrolein are added all at once to a mixture, stirred at 40° C., of 211.2 g (1.2 moles) of 2-hydrazino-4(3H)-quinazolinone, 1.5 litres of water, 540 ml of methanol and 220 ml of concentrated hydrochloric acid. The suspension is stirred at 40° for a total of 4.5 hours and at 60° for 1.5 hours. The crude 2-(4-methyl-1H-pyrazol-1-yl)-4(3H)-quinazolinone isolated at room temperature is obtained in an amount of 245 g of melting point 169°-71°.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 149.2 g (1.32 moles) of 2-methyl-3-dimethylaminoacrolein are added all at once to a mixture, stirred at 40° C., of 211.2 g (1.2 moles) of 2-hydrazino-4(3H)-quinazolinone, 1.5 litres of water, 540 ml of methanol and 220 ml of concentrated hydrochloric acid. The suspension is stirred at 40° for a total of 4.5 hours and at 60° for 1.5 hours. The crude 2-(4-methyl-1H-pyrazol-1-yl)-4(3H)-quinazolinone isolated at room temperature is obtained in an amount of 245 g of melting point 169°-71°.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture from Example 105A (1.56 g, 10.1 mmol), 3-dimethylamino-2-methyl-2-propenal (1.63 g, 14.4 mmol) and acetic acid (25 μL, 0.44 mmol) in ethanol (10 mL) was heated by microwave to 150° C. for 30 minutes. The mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (EtOAc, Rf=0.53) afforded 1.66 g (80%) of the title compound. MS (DCI) m/z 205 (M+H)+. concentrated Purification by silica gel chromatography (EtOAc, Rf=0.53)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Amino-4-bromopyrazole (0.331 g, 2.04 mmol) and 3-(dimethylamino)-2-methyl-2-propenal (0.220 g, 1.94 mmol) were dissolved in acetic acid (6.48 mL) and ethanol (9.72 mL) and the reaction stirred at room temperature for 16 h. Solvents were removed under reduced pressure. The remaining residue was taken up in dichloromethane and purified by column chromatography (20-80% EtOAc/Hex) to give the title compound (0.294 g, 1.39 mmol). LRMS (APCI) calc'd for (C7H6BrN3) [M+H]+, 212.0; found 211.9. 1H NMR (500 MHz, cdcl3) δ 8.44 (s, 2H), 8.04 (s, 1H), 2.40 (s, 3H). Solvents were removed under reduced pressure purified by column chromatography (20-80% EtOAc/Hex)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 149.2 g (1.32 moles) of 2-methyl-3-dimethylaminoacrolein are added all at once to a mixture, stirred at 40° C., of 211.2 g (1.2 moles) of 2-hydrazino-4(3H)-quinazolinone, 1.5 litres of water, 540 ml of methanol and 220 ml of concentrated hydrochloric acid. The suspension is stirred at 40° for a total of 4.5 hours and at 60° for 1.5 hours. The crude 2-(4-methyl-1H-pyrazol-1-yl)-4(3H)-quinazolinone isolated at room temperature is obtained in an amount of 245 g of melting point 169°-71°.