Benzo-1,3-dioxole-5-methylamine → 2-Benzyloxy-4-(4-methylenedioxybenzyl)amino-6-methoxyquinazoline

HRID 1900652Notes

Reaction equation

HRID 1900652 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.[CH2:12]([O:19][C:20]1[N:29]=[C:28](OCC2C=CC=CC=2)[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:38][CH3:39])[CH:26]=2)[N:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O>[CH2:12]([O:19][C:20]1[N:29]=[C:28]([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:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:38][CH3:39])[CH:26]=2)[N:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 187967462,4-Bisbenzyloxy-6-methoxyquinazoline

Product 1

HCID 214693442-Benzyloxy-4-(4-methylenedioxybenzyl)amino-6-methoxyquinazolineYield 17.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.25 g (8.27 mmol) of piperonylamine was added to a solution of 1.00 g (2.69 mmol) of the 2,4-bisbenzyloxy-6-methoxyquinazoline prepared in Example 90 in dimethyl sulfoxide (10 ml). The obtained mixture was stirred at 160° to 180° 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 0.20 g of the title compound as a colorless needle.

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-fa7cfa3775784d98bb6f35e9ee2564e4
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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