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

HRID 585093Notes

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. over night. 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 MHz, DMSO) δ 4.59-4.63 (d, 2H), 5.98 (s, 2H), 6.86 (s, 2H), 6.96 (s, 1H), 7.62-7.66 (d, 1H), 7.79-7.84 (d, 1H), 8.46 (s, 1H), 9.24-9.28 (t,1H).

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-f71b336ecbd14ceb93b756c708a78a53
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930113B2

Reaction notes

Loading…