N,N-Diethylaniline → 4-Chloro-5-methoxy-2-(methylsulfanyl)pyrimidine

HRID 658083ノート

反応式

HRID 658083 の反応式
[CH3:1][O:2][C:3]1[C:4](O)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:14])=O.C(N(CC)C1C=CC=CC=1)C>C(#N)C>[Cl:14][C:4]1[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=1

参加物

5

反応物 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178493801HCID 178493801、化合物

生成物 1

HCID 2435114-Chloro-5-methoxy-2-(methylsulfanyl)pyrimidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

5-Methoxy-2-methylsulfanyl-pyrimidin-4-ol (250 mg) is dissolved in acetonitrile (7 ml) and thereto are added phosphorus oxychloride (0.7 ml) and N,N-diethyl aniline (460 μl) and the mixture is heated under reflux for 5.5 hours. The reaction solution is evaporated azeotropically with toluene three times, and to the residue are added aqueous citric acid solution and chloroform, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3) to give 4-chloro-5-methoxy-2-methylsulfanyl-pyrimidine (260 mg). MS (m/z): 191/193 [M+H]+

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5.5 hours
  3. customThe reaction solution is evaporated azeotropically with toluene three times
  4. additionto the residue are added aqueous citric acid solution and chloroform
  5. customthe mixture is separated
  6. washThe organic layer is washed with a saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3)

出典と根拠

ORDレコード
ord-277f5048c1074e8584a00adab101b807
出典データセット
uspto-grants-2011_12
特許番号
US08076364B2

反応ノート

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