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

HRID 871422Notes

Reaction equation

HRID 871422 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-bfcb05f754e94679843d24d894912290
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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