Ethanol → 6-Amino-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline

HRID 55018Notes

Reaction equation

HRID 55018 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2[N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([N+:35]([O-])=O)[CH:31]=3)[N:26]([CH3:38])[C:25]2=[O:39])[CH2:20][CH2:19]1>[Fe].O>[NH2:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:38])[C:25](=[O:39])[N:24]([CH:21]1[CH2:20][CH2:19][N:18]([C:9]3[C:8]4[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([O:5][CH3:4])[CH:7]=4)[N:12]=[CH:11][N:10]=3)[CH2:23][CH2:22]1)[C:33]2=[O:34]

Participants

5

Reactant 2

HCID 702EthanolHCID 229235503-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-methyl-6-nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 229233356-Amino-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazolineYield 63%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

In a solvent mixture of 15 ml of ethanol and 5 ml of water was dissolved 500 mg (1.02 mmol) of Compound 1 obtained in Example 1, and 500 mg of iron and a catalytic amount of ferric chloride were added thereto, followed by heating under reflux for 1 hour. The reaction mixture was filtered while hot by using a filter aid, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed and dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1) and recrystallized from ether to give 275.2 mg (yield: 63%) of Compound 14 as pale yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. filtrationThe reaction mixture was filtered while hot
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionextracted with chloroform
  7. washThe organic layer was washed
  8. customdried
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
  11. customrecrystallized from ether

Sources & evidence

ORD record
ord-cd5ee0385d804a148e65a90023317280
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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