2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(3-fluoro-4-(hexylamino)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56179ノート

反応式

HRID 56179 の反応式
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C[Al](C)C.[NH:20](/[C:24](/[CH3:30])=[CH:25]\[C:26](OC)=[O:27])[C:21]([CH3:23])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:26](=[O:27])[CH:25]=[C:24]([CH3:30])[N:20]=[C:21]2[CH3:23])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参加物

5

反応物 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 641829002-fluoro-N1-hexylbenzene-1,4-diamine

生成物 1

HCID 729500023-(3-fluoro-4-(hexylamino)phenyl)-2,6-dimethylpyrimidin-4(3H)-one収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-fluoro-N1-hexylbenzene-1,4-diamine (3.36 g, 16 mmol) in CH2Cl2 (20 mL) was added trimethylaluminium (40 mL, 80 mmol, 2 M in toluene) slowly. The mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (3.02 g, 19.2 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 72 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (150 mL×3). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as pale yellow oil (1.57 g, 31%). The compound was characterized by the following spectroscopic data:

後処理

  1. stirringThe reaction mixture was stirred at rt for 72 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (150 mL×3)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

出典と根拠

ORDレコード
ord-f3d7dec2d63d43b18c85bfa4f22ef3ad
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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