Sodium Hydroxide → HCID 57654610, compound

HRID 1921645Notes

Reaction equation

HRID 1921645 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6](=[O:33])[CH:7]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][N:17]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:16]2=[O:32])C(OCC)=O)C>CO>[CH3:3][O:5][C:6](=[O:33])[CH2:7][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][N:17]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[C:16]2=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57654588HCID 57654588, compound

Product 1

HCID 57654610HCID 57654610, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide [2N] (0.59 mL) was added to a solution of 2-[3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-malonic acid diethyl ester (0.250 g, 0.590 mmol) in methanol (5 mL) and stirred at room temperature for several hours. The crude reaction was then evaporated in vacuo, 1N HCl was added and the product was extracted with ethyl acetate to give 0.141 g of [3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid methyl ester. This was dissolved in a mixture of toluene/methanol [8/1] (3 mL) and trimethylsilyldiazomethane [2.0M] (0.22 mL) was added at room temperature and stirred until bubbling has stopped. The reaction was then evaporated in vacuo and purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.119 g (60%) of [3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid methyl ester. Mass spectrum (LCMS, ESI pos.): Calcd for C19H18N2O4; found: 339.1, 340.1 (M+H).

Workup

  1. customThe crude reaction
  2. customwas then evaporated in vacuo, 1N HCl
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-0917f106cbc0401d8d96c909281fbaeb
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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