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

HRID 1498767ノート

反応式

HRID 1498767 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6a7ffe6cc5604f88b38e15c46083f7e9
出典データセット
uspto-grants-2015_12
特許番号
US09199990B2

反応ノート

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