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

HRID 2068031Notes

Reaction equation

HRID 2068031 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-e4eceac8004f4068a9e06d1e737d3e81
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

Loading…