3-(6-(Benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline → 4-(3-Aminophenoxy)-7-methoxyquinazolin-6-ol

HRID 1917821Notes

Reaction equation

HRID 1917821 reaction equation
C([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]2[O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[NH2:25][C:24]1[CH:23]=[C:22]([CH:28]=[CH:27][CH:26]=1)[O:21][C:12]1[C:11]2[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

4

Reactant 1

HCID 668775223-(6-(Benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline

Product 1

HCID 668761074-(3-Aminophenoxy)-7-methoxyquinazolin-6-olYield 74.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 3-(6-(benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline (3.64 g, 0.00974 mol) and Pd/C (10%) in ethanol/THF (400 mL, 3/1) was hydrogenated at 1 atm. of H2, at 50-55° C. for 3 h. The mixture was filtered through Celite and the filtrate was concentrated to about 100 mL. The crude was left in the fridge overnight. The solid was filtered and washed with small portion of cold ethanol to afford 4-(3-aminophenoxy)-7-methoxyquinazolin-6-ol (2.05 g, 74.3% yield). 1HNMR (DMSO-d6): δ 10.30 (1H, s), 8.49 (1H, s), 7.46 (1H, s), 7.34 (1H, s), 7.07 (1H, m), 6.48 (1H, m), 6.40 (2H, m), 5.29 (2H, s), 3.90 (3H, s). LC-MS (ESI) m/z 284 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated to about 100 mL
  3. waitThe crude was left in the fridge overnight
  4. filtrationThe solid was filtered
  5. washwashed with small portion of cold ethanol

Sources & evidence

ORD record
ord-721b563ef24f47eda9aa5f6d82594160
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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