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

HRID 336782노트

반응식

HRID 336782 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-3050a56a6aeb4d1ba9f11e53fc425dd2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889698B2

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