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Ethanol → 6-(5-Carboxy-naphthalen-2-yloxy)-pyrimidine-4-carboxylic acid ethyl ester

HRID 1094516
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인쇄 미리보기

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HRID 1094516 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.C[CH2:23][OH:24].CCN([CH2:30][CH3:31])CC.[C]=[O:33]>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:30]([O:33][C:23]([C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:19]([OH:21])=[O:20])[CH:10]=2)[N:5]=[CH:6][N:7]=1)=[O:24])[CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 248238946-(6-Chloropyrimidin-4-yloxy)-1-naphthoic acidHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 591759676-(5-Carboxy-naphthalen-2-yloxy)-pyrimidine-4-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 10 g (33.3 mMol) 6-(6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (preparation see WO 2006/59234; Step 25.1), 150 ml EtOH, 9.03 ml (64:9 mMol) Et3N and 2.35 g (3.32 mMol) PdCl2(PPh3)2 is stirred under a atmosphere of 120 bar carbonmonoxide in an autoclave for 12 h at 115° C. The reaction mixture is diluted with 400 ml EtOAc, filtered through Hyflo and the residue washed with MeOH. The filtrate is concentrated and the residue suspended in 400 ml EtOAc and 200 ml water. Acidification to pH 4 with 4 N HCl and addition of MeOH produces a solution. The aq. layer is separated off and extracted with 3 portions of EtOAc. The organic phases are washed with water and brine, dried (Na2SO4), treated with char coal and concentrated. Trituration of the residue in EtOAc/ether and filtration gives the title compound: m.p.: 211-212° C.; MS: [M+1]+=339.

후처리

  1. filtrationfiltered through Hyflo
  2. washthe residue washed with MeOH
  3. concentrationThe filtrate is concentrated
  4. additionAcidification to pH 4 with 4 N HCl and addition of MeOH
  5. customproduces a solution
  6. customThe aq. layer is separated off
  7. extractionextracted with 3 portions of EtOAc
  8. washThe organic phases are washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. additiontreated with char coal
  11. concentrationconcentrated
  12. filtrationTrituration of the residue in EtOAc/ether and filtration

출처 및 근거

ORD 기록
ord-6d870cb2a97b4b859419db8a671ae1d1
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133886B2

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