Cyanoacetamide → 4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 577442ノート

反応式

HRID 577442 の反応式
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C(O[K])(C)(C)C.[Si:13]([O:20][CH2:21][C:22]#[C:23][C:24](=O)[CH3:25])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CS(C)=O>[Si:13]([O:20][CH2:21][C:22]1[CH:23]=[C:24]([CH3:25])[NH:6][C:4](=[O:5])[C:3]=1[C:1]#[N:2])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 7898CyanoacetamideHCID 12764994HCID 12764994、化合物HCID 178418922HCID 178418922、化合物

生成物 1

HCID 682948094-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile収率 86.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 2-cyanoacetamide (1.74 g, 20.7 mmol) and tBuOK (2.32 g, 20.7 mmol) in DMSO (48 mL) was added 5-{[tert-butyl(dimethyl)silyl]oxy}pent-3-yn-2-one (Cpd G, 4.4 g, 21.0 mmol) dropwise. The reaction mixture turned bright orange. The reaction mixture was stirred for 2 hours at 0° C., then quenched with NH4Cl (sat., aq.) and diluted with water causing solids to precipitate out. The solids were collected via filtration and dried under vacuum to give 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cpd H, 5.0 g, 86%) as a tan solid.

後処理

  1. customquenched with NH4Cl (sat., aq.)
  2. additiondiluted with water causing solids
  3. customto precipitate out
  4. filtrationThe solids were collected via filtration
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-8edd1469bcfb4be1b0f7980c8d1e45c2
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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