HCID 136379399, compound → HCID 136262659, compound

HRID 591589Notes

Reaction equation

HRID 591589 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:34])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)=[CH:17][CH:16]=1)=[N:8]2.[H][H]>CCO.CC(O)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:34])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:25][CH2:26]3)=[CH:17][CH:16]=1)=[N:8]2

Participants

6

Reactant 2

HCID 136379399HCID 136379399, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136262659HCID 136262659, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (10) (0.34 mmol) in EtOH (10 mL) and HOAc (5 mL) was purged with nitrogen and 10% Pd/C (0.016 g) was added. The mixture was stirred under 1 atmosphere of hydrogen overnight. Then, the solution was filtered through Celite, with MeOH washings, and the filtrate was concentrated in vacuo. The material was purified by flash chromatography on silica gel to afford tert-butyl 4-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)piperidine-1-carboxylate (11).

Workup

  1. additionwas added
  2. filtrationThen, the solution was filtered through Celite, with MeOH washings
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7ed9140755ee4952918e47f8bbc9f8ee
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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