4-Bromo-1-methoxy-2-(trifluoromethyl)benzene → 4-(4-Methoxy-3-(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile

HRID 733192노트

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HRID 733192 반응식
[CH2:1]([C:4]1[CH:9]=[C:8]([Sn](C)(C)C)[N:7]=[C:6]([C:14]#[N:15])[N:5]=1)[CH2:2][CH3:3].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:8]2[CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]=[C:6]([C:14]#[N:15])[N:7]=2)=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26]

참가 물질

5

반응물 2

HCID 27753044-Bromo-1-methoxy-2-(trifluoromethyl)benzeneHCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile

생성물 1

HCID 498624724-(4-Methoxy-3-(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile수율 11.7%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Bis(triphenylphosphine)palladium dichloride (34 mg, 0.05 mmol) was added under a nitrogen atmosphere to a mixture of 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (150 mg, 0.48 mmol) and 4-methoxy-3-trifluoromethyl-bromobenzene (148 mg, 0.58 mmol) in dimethylformamide (3 mL). The mixture was heated for 5 hours at 80° C. then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent Cyclohexane/DCM 7/3) to afford a solid which was triturated in pentane. After filtration, 4-(4-methoxy-3-trifluoromethyl-phenyl)-6-propyl-pyrimidine-2-carbonitrile (18 mg, 11%) was obtained as an off white solid.

후처리

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customThe residue was chromatographed over silica gel (eluent Cyclohexane/DCM 7/3)
  6. customto afford a solid which
  7. customwas triturated in pentane
  8. filtrationAfter filtration

출처 및 근거

ORD 기록
ord-a9d80b6fad584e33b7f31fdd07669c47
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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