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

HRID 1094516
ノート
印刷プレビュー

反応式

HRID 1094516 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 248238946-(6-Chloropyrimidin-4-yloxy)-1-naphthoic acidHCID 178418416HCID 178418416、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6d870cb2a97b4b859419db8a671ae1d1
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08133886B2

反応ノート

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