Tributylphosphine → 4'-[(1-{[5-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methyl}-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1718819노트

반응식

HRID 1718819 반응식
[CH3:1][C:2]1[NH:3][C:4](=[O:26])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[Si:58]([O:65][CH2:66][C:67]1[CH:68]=[CH:69][C:70]([CH2:73]O)=[N:71][CH:72]=1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]>O1CCCC1>[Si:58]([O:65][CH2:66][C:67]1[CH:68]=[CH:69][C:70]([CH2:73][N:3]2[C:4](=[O:26])[C:5]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:14][CH:13]=3)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=[C:2]2[CH3:1])=[N:71][CH:72]=1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:59])[CH3:60]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 224732225-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridineHCID 1354272734'-[(2-Methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

생성물 1

HCID 574607604'-[(1-{[5-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methyl}-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile수율 53.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4′-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.6 g), 1,1′-(azodicarbonyl)dipiperidine (0.48 g), tributylphosphine (0.95 g), [5-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methanol (0.48 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.54 g, 49%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-43773df7cc9243098c65dacae4209cb0
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803940B2

반응 노트

불러오는 중…