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Ethyl Acetate → 5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine

HRID 1766081
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HRID 1766081 반응식
[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[N:5][C:6]([S:11][CH3:12])=[N:7][C:8]=1[CH:9]=[CH2:10])#[N:2].[C:21](=[O:24])([O-:23])[O-].[K+].[K+].[CH2:27](C(CC)(C([O-])=O)C([O-])=O)[CH3:28].[CH3:38][CH2:39][O:40][C:41]([CH3:43])=[O:42]>C(O)C.C1(C)C=CC=CC=1.Cl>[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[N:5][C:6]([S:11][CH3:12])=[N:7][C:8]=1[CH2:9][CH2:10][CH:43]([C:41]([O:40][CH2:39][CH3:38])=[O:42])[C:21]([O:23][CH2:27][CH3:28])=[O:24])#[N:2]
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참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69515632,2-DiethylpropanedioateHCID 211090865-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine

생성물 1

HCID 211090855-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine

시약·촉매·용매 3

HCID 313
Hydrochloric Acid
용매
HCID 702Ethanol용매
HCID 1140Toluene용매

실험 절차

5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine (example 25a) was dissolved in a mixture of ethanol (2 ml) and toluene (2 ml). Potassium carbonate (690 mg) and diethylmalonate (272 μl) were added and the mixture was stirred at room temperature for 4 h. The reaction mixture was then poured in a mixture of 0.5M aq. HCl (25 ml) and EtOAc (50 ml). The organic layer was washed with H2O (50 ml) and sat. aq. NaCl (50 ml), dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with toluene/EtOAC=100/0 to 95/5 (v/v) as eluent.

후처리

  1. washThe organic layer was washed with H2O (50 ml) and sat. aq. NaCl (50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by chromatography on silica gel with toluene/EtOAC=100/0 to 95/5 (v/v) as eluent

출처 및 근거

ORD 기록
ord-22c5850948a84a268cdf232a3a50e7e0
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07229990B2

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