2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2,6-dimethyl pyrimidin-4(3H)-one

HRID 56159ノート

反応式

HRID 56159 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][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C[Al](C)C.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]2[CH3:25])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 176096902-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamine

生成物 1

HCID 729498333-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2,6-dimethyl pyrimidin-4(3H)-one収率 69.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamine (0.50 g, 2.09 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (3.2 mL, 6.40 mmol, 2 M in toluene) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (0.65 g, 4.13 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt for 36 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=30:1) to give the title compound as a white solid (0.50 g, 24%). The compound was characterized by the following spectroscopic data:

後処理

  1. stirringThe reaction mixture was stirred at rt for 36 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (100 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=30:1)

出典と根拠

ORDレコード
ord-738b2cbda2a04d41a39f2d384bb3c46c
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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