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

HRID 577442노트

반응식

HRID 577442 반응식
[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]

참가 물질

5

반응물 3

HCID 7898CyanoacetamideHCID 12764994HCID 12764994, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8edd1469bcfb4be1b0f7980c8d1e45c2
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

반응 노트

불러오는 중…