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7-Benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline → 7-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline

HRID 454055
Notes
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Reaction equation

HRID 454055 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24]([CH3:29])=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.[H][H]>C(Cl)Cl.CN(C=O)C.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24]([CH3:29])=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 220308047-Benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1357631087-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazolineYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (0.2 g, 0.5 mmol), (prepared as described in Example 48), in a mixture of methylene chloride (5 ml) and DMF (2 ml) containing 10% palladium-on-charcoal (50 mg) was treated with hydrogen at 1.8 atmospheres pressure for 2 hours. The suspension was filtered and the catalyst was washed with methanol followed by methylene chloride. The volatiles were removed from the filtrate by evaporation. The residue was triturated with water. The resulting solid was washed with water and dried under vacuum over phosphorus pentoxide at 60° C. to give 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (140 mg, 89%).

Workup

  1. filtrationThe suspension was filtered
  2. washthe catalyst was washed with methanol
  3. customThe volatiles were removed from the filtrate by evaporation
  4. customThe residue was triturated with water
  5. washThe resulting solid was washed with water
  6. dry with materialdried under vacuum over phosphorus pentoxide at 60° C.

Sources & evidence

ORD record
ord-12f5a6baa50e4d0abd19fba7d3906f3a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492560B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes