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6-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester → 6-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094511
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인쇄 미리보기

반응식

HRID 1094511 반응식
[CH3:1][O:2][Na].[CH3:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH2:25]Br)[N:20]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7]>CO.CCOC(C)=O.O>[CH3:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][O:2][CH3:1])[N:20]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 666399346-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl esterHCID 178418582HCID 178418582, 화합물

생성물 1

HCID 591759856-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

760 μl (4.12 mMol) of a 5.4 M solution of MeONa in MeOH are added to a solution of 1.28 g (3.43 mMol) 6-(2-bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester in 70 ml MeOH. After 22 h stirring at rt, the mixture is diluted with EtOAc and water, the aq. layer separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 19: 1→1:3) gives the title compound: MS: [M+1]+=325; 1H NMR (CDCl3): δ ppm 9.06 (d, 1H), 8.66 (d, 1H), 8.24 (d, 1H), 8.03 (d, 1H), 7.70 (s, 1H), 7.59 (t, 1H), 7.46 (d, 1H), 6.82 (d, 1H), 4.58 (s, H2C), 4.06 (s, H3C), 3.53 (s, H3C).

후처리

  1. customthe aq. layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c82066a178e547c4bd6fd99f9f36edd5
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133886B2

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