Benzo-1,3-dioxole-5-methylamine → HCID 18796703, compound

HRID 1003506Notes

Reaction equation

HRID 1003506 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14]1[N:23]=[C:22](OC)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:26][CH3:27])[CH:20]=2)[N:15]=1>>[CH3:12][O:13][C:14]1[N:23]=[C:22]([NH:11][CH2:1][C:2]2[CH:10]=[CH:9][C:8]3[O:7][CH2:6][O:5][C:4]=3[CH:3]=2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:26][CH3:27])[CH:20]=2)[N:15]=1

Participants

3

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 18796677HCID 18796677, compound

Product 1

HCID 18796703HCID 18796703, compoundYield 18%

Conditions

Temperature
155 °C

Procedure

3.75 g (24.8 mmol) of piperonylamine was added to a solution of 2.00 g (8.26 mmol) of the 2,4,6-trimethoxyquinazoline prepared in Example 88 in dimethyl sulfox (15 ml). The obtained mixture was stirred under heating at 150 to 160° C. After one hour, the reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 0.50 g of the title compounds as a pale-yellow crystal.

Workup

  1. customthe reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  2. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-3cd1c31c7b2b4d87a07466f6c63553ef
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

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