(2-Methoxy-4,6-dimethylphenyl)boronic acid → HCID 22490043, 화합물

HRID 2180005노트

반응식

HRID 2180005 반응식
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([CH3:11])[N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:15]=1B(O)O>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:6]1[C:5]([OH:10])=[C:4]([CH3:11])[N:3]=[C:2]([C:15]2[C:14]([O:13][CH3:12])=[CH:19][C:18]([CH3:20])=[CH:17][C:16]=2[CH3:21])[N:7]=1

참가 물질

7

반응물 2

HCID 21931520(2-Methoxy-4,6-dimethylphenyl)boronic acidHCID 22490069HCID 22490069, 화합물

생성물 1

HCID 22490043HCID 22490043, 화합물

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

반응 조건

온도
95 °C

실험 절차

A mixture of 2-chloro-4-methoxy-6-methylpyrimidin-5-ol (348 mg, 2.0 mmol), 2-methoxy-4,6-dimethylphenylboronic acid (540 mg, 3.0 mmol), tetrakis(triphenylphosphine)palladium (0) (115 mg, 5 mol %) in toluene (12 mL) and sodium carbonate (1M in water, 4 mL) is heated at 95° C. (oil bath temperature) in a pressure tube for 14 hours. The reaction is cooled to room temperature, diluted with ethyl acetate, washed with NaOH (2M) and then brine (2×50 mL). The solvents are dried (sodium sulfate) and removed under reduced pressure. Flash chromatography of the crude product (50% ethyl acetate in hexanes) yields 4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ol as a white solid.

후처리

  1. temperatureThe reaction is cooled to room temperature
  2. washwashed with NaOH (2M)
  3. dry with materialThe solvents are dried (sodium sulfate)
  4. customremoved under reduced pressure

출처 및 근거

ORD 기록
ord-d8fc84db2620473d8f40827898f1aadb
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887875B2

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