Ammonium formate → 5-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-one

HRID 555572노트

반응식

HRID 555572 반응식
C([O-])=O.[NH4+].C([O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]2[NH:29][C:28](=[O:30])[C:27]3[C:22](=[CH:23][C:24]([O:32][CH3:33])=[CH:25][C:26]=3[OH:31])[N:21]=2)=[CH:15][C:14]=1[CH3:34])C1C=CC=CC=1>CN(C=O)C.[C].[Pd]>[OH:31][C:26]1[CH:25]=[C:24]([O:32][CH3:33])[CH:23]=[C:22]2[C:27]=1[C:28](=[O:30])[NH:29][C:20]([C:16]1[CH:17]=[C:18]([CH3:19])[C:13]([OH:12])=[C:14]([CH3:34])[CH:15]=1)=[N:21]2

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 1363988572-(4-benzyloxy-3,5-dimethyl-phenyl)-5-hydroxy-7-methoxy-3H-quinazolin-4-one

생성물 1

HCID 1360379705-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-one수율 74%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

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. temperatureThe resulting suspension was cooled to room temperature
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated
  4. additionthe residue was diluted with water (20 mL)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with hexanes

출처 및 근거

ORD 기록
ord-dc697f8a737f4b19b6783bf4beca8121
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053440B2

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