Sodium Carbonate → 4-((3,4-(Methylenedioxy)benzyl)amino)-6,7,8-trimethoxyquinazoline

HRID 1938512Notes

Reaction equation

HRID 1938512 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:18]([NH2:28])[C:19]1[CH:27]=[CH:26][C:25]2[O:24][CH2:23][O:22][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[CH2:23]1[O:24][C:25]2[CH:26]=[CH:27][C:19]([CH2:18][NH:28][C:2]3[C:11]4[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:20][C:21]=2[O:22]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 1006864-Chloro-6,7,8-trimethoxyquinazoline

Product 1

HCID 2059644-((3,4-(Methylenedioxy)benzyl)amino)-6,7,8-trimethoxyquinazolineYield 69.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

21.2 g (0.083 mol) of 4-chloro-6,7,8-trimethoxyquinazoline, 17.0 g (0.112 mol) of piperonylamine and 13.5 g (0.127 mol) of sodium carbonate were mixed with 400 ml of isopropyl alcohol. The obtained mixture was heated under reflux for 24 hours and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate to give 21.3 g of the title compound as a pale-yellow needle.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 24 hours
  3. distillationdistilled under a reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fc0388eb482446ab932bcd40631faa53
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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