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

HRID 733192ノート

反応式

HRID 733192 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9d80b6fad584e33b7f31fdd07669c47
出典データセット
uspto-grants-2009_09
特許番号
US07589095B2

反応ノート

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