HCID 136390988, compound → HCID 67282748, compound

HRID 1616137Notes

Reaction equation

HRID 1616137 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]([O:18]CC2C=CC=CC=2)=[O:17])[NH:3]1>CO.C(OCC)(=O)C.[Pd]>[CH3:15][O:14][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[O:1])[NH:3][CH:4]([C:16]([OH:18])=[O:17])[NH:5]2)=[CH:10][CH:9]=1)=[O:13]

Participants

5

Reactant 1

HCID 136390988HCID 136390988, compound

Product 1

HCID 67282748HCID 67282748, compoundYield 95.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzyl 7-methyl 4-oxo-3,4-dihydroquinazoline-2,7-dicarboxylate (0.70 g, 2.0 mmol) in methanol (7 mL) and ethyl acetate (4 mL) was added 10% palladium on carbon (20 mg). The mixture was purged with H2 gas (3×) and stirred under an atmosphere of H2 for 1 d. The reaction mixture was then filtered through Celite, washed with MeOH and concentrated to afford 7-(methoxycarbonyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-2-carboxylic acid (0.48 g, 90%). LC-MS: (FA) ES+ 251; 1H NMR (400 MHz, DMSO) δ 7.66 (d, J=8.0 Hz, 1H), 7.52 (s, 1H), 7.17 (d, J=8.2 Hz, 1H), 4.65 (s, 1H), 3.82 (s, 3H).

Workup

  1. customThe mixture was purged with H2 gas (3×)
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washwashed with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-993898147ecf48d99981267aa0c429bc
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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