Methyl iodide → 3-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-methyl-6-nitro-2,4(1H,3H)-quinazolinedione

HRID 55005Notes

Reaction equation

HRID 55005 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]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=3)[NH:23][C:22]2=[O:35])[CH2:17][CH2:16]1.[H-].[Na+].[CH3:38]I.[Cl-].[NH4+]>CN(C=O)C>[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]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=3)[N:23]([CH3:38])[C:22]2=[O:35])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 229233993-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline2×

Product 1

HCID 229235503-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-methyl-6-nitro-2,4(1H,3H)-quinazolinedioneYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 1 ml of DMF was dissolved 239 mg (0.5 mmol) of 3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline (Compound 24) obtained in Reference Example 6, and the solution was added dropwise to a solution of 22 mg (0.55 mmol) of 60% sodium hydride in 2 ml of DMF under ice cooling. After stirring for 20 minutes, 0.031 ml (0.5 mmol) of methyl iodide was added thereto, followed by stirring at room temperature for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water, dried by heating, and recrystallized from ethanol/ether to give 152.9 mg (yield: 62%) of Compound 1 as pale yellow crystals.

Workup

  1. customobtained in Reference Example 6
  2. stirringby stirring at room temperature for 1 hour
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe solid was washed with water
  5. customdried
  6. temperatureby heating
  7. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-defb9286099445b2b0779c7c3dac8f9d
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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