Ethanol → 4-(3-Aminophenyl)-6,7-dimethoxy-2-methylaminoquinazoline

HRID 275733Notes

Reaction equation

HRID 275733 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([NH:15][CH3:16])[N:7]=[C:6]2[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=1.C(N(CC)CC)C.C(O)C.[H][H]>[C].[Pd].O1CCCC1>[NH2:23][C:19]1[CH:18]=[C:17]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[C:8]([NH:15][CH3:16])[N:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 12150401HCID 12150401, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 155405314-(3-Aminophenyl)-6,7-dimethoxy-2-methylaminoquinazolineYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.83 g of 6,7-dimethoxy-2-methylamino-4-(3-nitrophenyl) quinazoline obtained in Production Example 4,200 mg of 10% palladium-carbon powder (hydrate) and 1.44 g triethylamine were suspended in a mixed solvent of 10 ml ethanol and 10 ml tetrahydrofuran. After the atmosphere was replaced with hydrogen, the mixture was stirred for 15 hours at ordinary pressure at room temperature. The reaction solution was filtered, then the filtrate was evaporated, and the crude product was purified and separated by silica gel column chromatography (hexane:ethyl acetate=1:3). The product was recrystallized from hexane-ethyl acetate to give 1.22 g of the title compound as pale yellow crystals.

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe filtrate was evaporated
  3. customthe crude product was purified
  4. customseparated by silica gel column chromatography (hexane:ethyl acetate=1:3)
  5. customThe product was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-00bcdbf9eef048c8985e26b5df30abbc
Source dataset
uspto-grants-2002_03
Patent number
US06352989B1

Reaction notes

Loading…