Benzo-1,3-dioxole-5-methylamine → 4-((1,3-Benzodioxol-5-ylmethyl)amino)-2,6-dichloro quinazoline
Reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[CH2:14]([NH2:24])[C:15]1[CH:23]=[CH:22][C:21]2[O:20][CH2:19][O:18][C:17]=2[CH:16]=1>C(O)C>[O:20]1[C:21]2[CH:22]=[CH:23][C:15]([CH2:14][NH:24][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=4)[N:3]=[C:2]([Cl:1])[N:11]=3)=[CH:16][C:17]=2[O:18][CH2:19]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
A solution of 2,4,6-trichloroquinazoline (0.186 g, 0.80 mmol) in ethanol (20 mL) was heated to 55° C. and piperonylamine (0.145 g, 0.96 mmol) was added. The resulting mixture was stirred at 55° C. overnight. Volatiles were evaporated and the residue was partitioned between methylene chloride and saturated solution of ammonium hydroxide. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 0.268 g (96 % yield) of the title compound as a white solid. 1H NMR (300 ÊMt, DMSO) δ4.59-4.63 (d, 2 H), 5.98 (s, 2 H), 6.86 (s, 2 H), 6.96 (s, 1 H), 7.62-7.66 (d, 1 H), 7.79-7.84 (d, 1 H), 8.46 (s, 1 H), 9.24-9.28 (t, 1 H).