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

HRID 631377Notes

Reaction equation

HRID 631377 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-4be9a2d87ebd4e828c817f0f13abca16
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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