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4'-[(5-bromo-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile → 4'-{[5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1674405
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HRID 1674405 반응식
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](B(O)O)[CH:10]=2)[O:5][C:4]([CH3:16])([CH3:15])[CH2:3]1.Br[C:18]1[C:23](=[O:24])[N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:28][CH:27]=2)[C:21]([CH2:40][CH2:41][CH3:42])=[N:20][C:19]=1[CH3:43]>O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:18]3[C:23](=[O:24])[N:22]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]5[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=5)=[CH:30][CH:31]=4)[C:21]([CH2:40][CH2:41][CH3:42])=[N:20][C:19]=3[CH3:43])[CH:10]=2)[O:5][C:4]([CH3:16])([CH3:15])[CH2:3]1
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참가 물질

7

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HCID 574601144'-[(5-bromo-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrileHCID 67201281(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)boronic acid

생성물 1

HCID 594694234'-{[5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile수율 76.4%

시약·촉매·용매 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8857Ethyl Acetate용매
HCID 10796Cesium carbonate용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of (4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)boronic acid (0.79 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.1 g) and 4′-[(5-bromo-4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (1 g) in 1,4-dioxane (10 mL) and 2 M cesium carbonate (4 mL) was stirred overnight at 100° C. under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.94 g, 76%).

후처리

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-35456444317443fea54c831feed15af8
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07998968B2

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