3-[1-(7-Benzyloxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline → 1,2,3,4-Tetrahydro-3-[1-(7-hydroxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,6-dimethyl-2,4-dioxo-quinazoline

HRID 55044Notes

Reaction equation

HRID 55044 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[C:34](=[O:35])[C:33]5[C:28](=[CH:29][CH:30]=[C:31]([CH3:36])[CH:32]=5)[N:27]([CH3:37])[C:26]4=[O:38])[CH2:21][CH2:20]3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:39][CH3:40])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[C:34](=[O:35])[C:33]5[C:28](=[CH:29][CH:30]=[C:31]([CH3:36])[CH:32]=5)[N:27]([CH3:37])[C:26]4=[O:38])[CH2:21][CH2:20]3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:39][CH3:40]

Participants

4

Reactant 1

HCID 229234363-[1-(7-Benzyloxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

Product 1

HCID 1358475911,2,3,4-Tetrahydro-3-[1-(7-hydroxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,6-dimethyl-2,4-dioxo-quinazolineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 10 ml of ethanol was dissolved 150 mg (0.28 mmol) of Compound 87 obtained in Example 66, and 30 mg of 10% palladium on carbon was added thereto, followed by vigorous stirring at room temperature for 6 hours under a hydrogen atmosphere at atmospheric pressure. The reaction mixture was filtered using a filter aid, and the filtrate was concentrated under reduced pressure. To the residue were added ethanol and ethyl acetate. The precipitated crystals were collected by filtration, washed, and dried to give 105.2 mg (yield: 84%) of Compound 89 as white crystals.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue were added ethanol and ethyl acetate
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-39777652ee9048599ae6885ccc5b8893
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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