Sodium Hydroxide → HCID 57654610, compound

HRID 1661821Notes

Reaction equation

HRID 1661821 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-336074c5d13845b29251ea3924ac6f10
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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