Toluene → 6-Methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1384667Notes

Reaction equation

HRID 1384667 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16](C)[C:17](C(C)(C)C)=O)[N:9]=[CH:8][N:7]([CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[C:6]2=[O:32].C1(C)C=CC=CC=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][NH:16][CH3:17])[N:9]=[CH:8][N:7]([CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])[C:6]2=[O:32]

Participants

5

Reactant 2

HCID 1140TolueneHCID 226249226-methoxy-7-(2-(N-methyl-N-(t-butylcarbonyl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 226249706-Methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 73.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-methoxy-7-(2-(N-methyl-N-(t-butylcarbonyl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.39 g, 3 mmol) in methylene chloride (4 ml) and TFA (4 ml) was stirred at ambient temperature for 1 hour. Toluene was added, and the volatiles were removed by evaporation. The residue was triturated with ether and the resulting solid was collected by filtration. The solid was dissolved in water, sodium hydrogen carbonate was added and the aqueous mixture was extracted with methylene chloride. The organic extract was dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether and the solid was collected by filtration to give 6-methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (800 mg, 73%). 1H NMR Spectrum: (DMSOd6; CF3COOD) 1.13(s, 9H); 2.72(s, 3H); 3.45(br s, 2H); 3.95(br s, 3H); 4.5(t, 2H); 5.94(s, 2H); 7.31(s, 1H); 7.6(s, 1H); 8.47(s, 1H) MS-ESI: 364 [MH]+

Workup

  1. customthe volatiles were removed by evaporation
  2. customThe residue was triturated with ether
  3. filtrationthe resulting solid was collected by filtration
  4. dissolutionThe solid was dissolved in water
  5. additionsodium hydrogen carbonate was added
  6. extractionthe aqueous mixture was extracted with methylene chloride
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was triturated with ether
  11. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-5fbd2a31adf84353b61a924f28448243
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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