Water → 4-(7-Azaindol-5-yloxy)-6-hydroxy-7-methoxyquinazohne

HRID 916387Notes

Reaction equation

HRID 916387 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:29][CH3:30])=[C:18]([O:21]CC5C=CC=CC=5)[CH:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:7][N:8]=2)[CH:3]=[CH:2]1.C([O-])=O.[NH4+].O>[Pd].CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:29][CH3:30])=[C:18]([OH:21])[CH:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:7][N:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 666467954-(7-Azaindol-5-yloxy)-6-benzyloxy-7-methoxyquinazoline

Product 1

HCID 589602364-(7-Azaindol-5-yloxy)-6-hydroxy-7-methoxyquinazohneYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(7-azaindol-5-yloxy)-6-benzyloxy-7-methoxyquinazoline (0.36 g, 0.873 mmol), ammonium formate (0.55 g, 8.73 mmol) and 10% palladium on carbon (0.05 g) in DMF (7 ml) containing water (0.3 ml) was stirred at ambient temperature for 1 hour. The mixture was filtered and the filtrate was evaporated. The residue was triturated under diethyl ether and the solid was filtered, washed with ether and dried under vacuum. The solid was triturated under water, filtered, washed with water and dried under vacuum over P2O5 to give 4-(7-azaindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline (0.26 g, 85%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated under diethyl ether
  4. filtrationthe solid was filtered
  5. washwashed with ether
  6. customdried under vacuum
  7. customThe solid was triturated under water
  8. filtrationfiltered
  9. washwashed with water
  10. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-a28e31fc1491469a92780ba862bb9083
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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