Potassium Carbonate → 4-(7-Azaindol-5-yloxy)-6-benzyloxy-7-methoxyquinazoline

HRID 2068030Notes

Reaction equation

HRID 2068030 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22][C:23]1[CH:24]=[C:25]2[C:29](=[N:30][CH:31]=1)[NH:28][CH:27]=[CH:26]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][C:12]3[C:11]4[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:10]=4)[N:15]=[CH:14][N:13]=3)=[CH:31][N:30]=2)[CH:26]=[CH:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 114265806-(Benzyloxy)-4-chloro-7-methoxyquinazolineHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-ol

Product 1

HCID 666467954-(7-Azaindol-5-yloxy)-6-benzyloxy-7-methoxyquinazolineYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-benzyloxy-4-chloro-7-methoxyquinazoline (0.449 g, 1.49 mmol), (EP1153920 production examples 28-30), 5-hydroxy-7-azaindole (0.22 g, 1.64 mmol) and potassium carbonate (0.28 g, 2.02 mmol) in DMF (5 ml) was stirred at 95° C. for 3 hours. The mixture was filtered and the filtrate was evaporated and dried overnight under vacuum. The residue was triturated under methylene chloride and ethyl acetate and the solid was filtered and dried under vacuum to give 4-(7-azaindol-5-yloxy)-6-benzyloxy-7-methoxyquinazoline (0.36 g, 60%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customdried overnight under vacuum
  4. customThe residue was triturated under methylene chloride
  5. filtrationethyl acetate and the solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-49267335c92a40cc995fee2091106731
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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