Thiophosgene → 5-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidine

HRID 1628513노트

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HRID 1628513 반응식
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([NH2:14])=[C:9]([CH3:15])[N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:14]([C:10]1[C:9]([CH3:15])=[N:8][C:7]([O:6][CH3:5])=[N:12][C:11]=1[CH3:13])=[C:1]=[S:2]

참가 물질

5

반응물 2

HCID 10040ThiophosgeneHCID 687393852-Methoxy-4,6-dimethylpyrimidin-5-amine

생성물 1

HCID 866328935-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidine수율 88%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

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온도
0 °C

실험 절차

Thiophosgene (1.8 mL, 23.6 mmol) was added dropwise to a stirred mixture of 2-methoxy-4,6-dimethylpyrimidin-5-amine (2.82 g, 18.4 mmol) in tetrahydrofuran (25 mL) and saturated aqueous sodium hydrogen carbonate (25 mL) at 0° C., and the mixture was stirred at 0° C. for 40 minutes. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether/n-hexane to give the title compound as a pale yellow powder (3.16 g, 16.2 mmol, 88%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether/n-hexane

출처 및 근거

ORD 기록
ord-e736bd3fcc62484c91a6ac605e8f2559
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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