3,5-Dimethylphenol → 2,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine

HRID 426097

反応式

HRID 426097 の反応式
[CH:1]([C:4]1[C:5]([Cl:12])=[N:6][C:7]([Cl:11])=[N:8][C:9]=1Cl)([CH3:3])[CH3:2].[CH3:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1.[H-].[Na+]>CN(C=O)C.CCOCC>[Cl:11][C:7]1[N:6]=[C:5]([Cl:12])[C:4]([CH:1]([CH3:3])[CH3:2])=[C:9]([O:21][C:16]2[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([CH3:13])[CH:15]=2)[N:8]=1

参加物

6

反応物 3

HCID 79483,5-DimethylphenolHCID 24758Sodium hydrideHCID 2490092,4,6-Trichloro-5-isopropylpyrimidine

生成物 1

HCID 189252522,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine収率 90.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-40 °C

実験手順

To a stirred mixture of 5-isopropyl-2,4,6-trichloropyrimidine (1) (23.68 g, 0.105M), 3,5-dimethylphenol (12.2 g, 0.2M) in anhydrous DMF (200 ml) cooled in a dry ice-acetone bath (−40° C.) under nitrogen atmosphere, was portionwise added 60% sodium hydride (4.2 g, 0.105M). The reaction temperature was then slowly raised to room temperature during 3 hr. The reaction mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a pale yellow solid. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 28 g (90%) of a white solid. m.p. 107-108° C.; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.0 Hz), 2.35 (6H, s), 3.58 (1H, m), 6.72 (2H, s), 6.91 (1H, s).

後処理

  1. temperatureThe reaction temperature was then slowly raised to room temperature during 3 hr
  2. washwashed with water twice
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a crude product as a pale yellow solid
  7. customThe crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9))

出典と根拠

ORDレコード
ord-043b973a320b43ec8ae62e73487fd6d0
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

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