HCID 21114609, compound → HCID 21114610, compound

HRID 749200Notes

Reaction equation

HRID 749200 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1>[Pd].CC(N(C)C)=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 21114609HCID 21114609, compound

Product 1

HCID 21114610HCID 21114610, compoundYield 43,221.801%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

10% palladium on carbon (56 g, 53 mmol) was added to a solution of tert-butyl 2-[7-(benzyloxy)-6-methoxy-4-oxo-3(4H)-quinazolinyl]acetate (562 g, 1.42 mmol) in dimethylacetamide (3500 ml) at ambient temperature and stirred for 3 hours under an atmosphere of hydrogen (1 bar). The reaction was filtered through a pad of celite and the solvent evaporated in vacuo. The residual solid was dissolved in 20% methanol in dichloromethane and passed through a pad of silica gel. Evaporation of the solvent in vacuo followed by trituration with methanol yielded, tert-butyl 2-[7-hydroxy-6-methoxy-4-oxo-3(4H)-quinazolinyl]acetate (188 g, 43% yield):

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residual solid was dissolved in 20% methanol in dichloromethane
  4. customEvaporation of the solvent in vacuo
  5. customyielded

Sources & evidence

ORD record
ord-fd2e409c651a4374bccbbe8390102bc7
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

Loading…