Nitrogen → 3-(3-fluoro-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56090

反応式

HRID 56090 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].C[Al](C)C.N#N.[NH:21](/[C:25](/[CH3:31])=[CH:26]\[C:27](OC)=[O:28])[C:22]([CH3:24])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:27](=[O:28])[CH:26]=[C:25]([CH3:31])[N:21]=[C:22]2[CH3:24])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 947NitrogenHCID 14853303-Fluoro-4-morpholinoanilineHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925Trimethylaluminum

生成物 1

HCID 729482043-(3-fluoro-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one収率 67.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-fluoro-4-morpholinoaniline (11.0 g, 56 mmol) in CH2Cl2 (200 mL) was added trimethylaluminium (168 mL, 168 mmol, 1 M in heptane) dropwise carefully under N2. The mixture was stirred at rt for 20 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (10.57 g, 67 mmol) in CH2Cl2 (30 mL). The reaction was stirred at rt for 5 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2. The combined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was recrystallized from EtOAc to give the title compound as a pale yellow solid (11.39 g, 67%). The compound was characterized by the following spectroscopic data:

後処理

  1. stirringThe reaction was stirred at rt for 5 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from EtOAc

出典と根拠

ORDレコード
ord-0c5eb14a07444697aec7fb0a52a6ebea
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

関連ノート

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