Magnesium Bromide → 2-(4-benzyloxy-3,5-dimethyl-phenyl)-5-hydroxy-7-methoxy-3H-quinazolin-4-one

HRID 555571Notes

Reaction equation

HRID 555571 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[NH:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][C:20]([O:29][CH3:30])=[CH:21][C:22]=3[O:27]C)[N:17]=2)=[CH:11][C:10]=1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Mg+2].[Br-]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[NH:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][C:20]([O:29][CH3:30])=[CH:21][C:22]=3[OH:27])[N:17]=2)=[CH:11][C:10]=1[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 1360379952-(4-benzyloxy-3,5-dimethyl-phenyl)-5,7-dimethoxy-3H-quinazolin-4-one

Product 1

HCID 1363988572-(4-benzyloxy-3,5-dimethyl-phenyl)-5-hydroxy-7-methoxy-3H-quinazolin-4-oneYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(4-benzyloxy-3,5-dimethyl-phenyl)-5,7-dimethoxy-3H-quinazolin-4-one (1.2 g, 2.92 mmol) and magnesium bromide (0.644 g, 3.5 mmol) in pyridine (50 mL) was stirred at reflux for 12 h. The mixture was concentrated and the solid residue was made into slurry with HCl (2 N, 100 mL). The solid was collected by filtration, washed with water and hexanes to yield 2-(4-benzyloxy-3,5-dimethyl-phenyl)-5-hydroxy-7-methoxy-3H-quinazolin-4-one as a white solid (0.76 g, 65%). A solution of ammonium formate (0.945 g, 15 mmol) and 2-(4-benzyloxy-3,5-dimethyl-phenyl)-5-hydroxy-7-methoxy-3H-quinazolin-4-one (0.1 g, 0.25 mmol) in DMF (50 mL) was mixed with palladium carbon (0.1 g) and stirred at 85° C. for 14 h. The resulting suspension was cooled to room temperature, passed through a Celite pad, and washed with DCM. The filtrate was concentrated and the residue was diluted with water (20 mL). The resulting solid was collected by filtration and washed with hexanes to afford 5-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-one (57 mg, 74%) as light yellow solid. Selected data: MS (ES) m/z: 312.94; MP 291.3-293° C.

Workup

  1. temperatureat reflux for 12 h
  2. concentrationThe mixture was concentrated
  3. filtrationThe solid was collected by filtration
  4. washwashed with water and hexanes

Sources & evidence

ORD record
ord-a57b35a414bc4000b2e53bcdb4df5a72
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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