Benzo-1,3-dioxole-5-methylamine → 4-((1,3-Benzodioxol-5-ylmethyl)amino)-2,6-dichloro quinazoline

HRID 993259Notes

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]1

Participants

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).

Workup

customVolatiles were evaporated
customthe residue was partitioned between methylene chloride and saturated solution of ammonium hydroxide
dry with materialThe organic phase was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3f0a2d225fd54ab691031df5889ac26f
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472425B1

Reaction notes

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