Nitrogen → 3-(3-fluoro-4-morpholinophenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one

HRID 56136

反応式

HRID 56136 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.[F:21][C:22]1[CH:23]=[C:24]([CH:37]=[CH:38][CH:39]=1)[O:25][CH2:26][C:27]([NH:29]/[C:30](/[CH3:36])=[CH:31]\[C:32](OC)=[O:33])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:32](=[O:33])[CH:31]=[C:30]([CH3:36])[N:29]=[C:27]2[CH2:26][O:25][C:24]2[CH:37]=[CH:38][CH:39]=[C:22]([F:21])[CH:23]=2)[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 16682925TrimethylaluminumHCID 90022556Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate

生成物 1

HCID 727221323-(3-fluoro-4-morpholinophenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one収率 62%

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 (0.55 g, 2.80 mmol) in anhydrous CH2Cl2 (40 mL) was added trimethylaluminium (2.0 mL, 4 mmol, 2 M in heptane) carefully under N2 at rt. The mixture was stirred at rt for 30 min, followed by the addition of a solution of methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate (0.75 g, 2.80 mmol) in anhydrous CH2Cl2 (10 mL). The reaction mixture was stirred for another 7 h, then quenched with an appropriate amount of water and washed with brine twice. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (0.24 g, 62%). The compound was characterized by the following spectroscopic data:

後処理

  1. stirringThe reaction mixture was stirred for another 7 h
  2. customquenched with an appropriate amount of water
  3. washwashed with brine twice
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

出典と根拠

ORDレコード
ord-c618f10bd48b4944b64bcc4cf5086fa4
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

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