Sodium Carbonate → HCID 18796651, compound

HRID 1938557Notes

Reaction equation

HRID 1938557 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:19]=[C:18](Cl)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:21][CH3:22])[CH:16]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:33])[C:24]1[CH:32]=[CH:31][C:30]2[O:29][CH2:28][O:27][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[CH2:1]([O:8][CH2:9][C:10]1[N:19]=[C:18]([NH:33][CH2:23][C:24]2[CH:32]=[CH:31][C:30]3[O:29][CH2:28][O:27][C:26]=3[CH:25]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:21][CH3:22])[CH:16]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 18796639HCID 18796639, compound

Product 1

HCID 18796651HCID 18796651, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.74 g (2.4 mmol) of the 2-benzyloxymethyl-4-chloro-6-methoxyquinazoline prepared in Example 246, 0.55 g (3.6 mmol) of piperonylamine and 0.50 g of sodium carbonate were mixed with 20 ml of isopropyl alcohol. The obtained mixture was heated under reflux. After 6 hours, the reaction mixture was distilled under a reduced pressure to remove the solvent and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) and recrystallized from chloroform/n-hexane to give 1.01 g of the title compound as a yellow crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux
  3. distillationthe reaction mixture was distilled under a reduced pressure
  4. customto remove the solvent
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  6. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-00da7781edd748efb09e06ccdf29bd7b
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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