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Methyl iodide → (E)-N-Methyl-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

HRID 235259
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HRID 235259 반응식
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH:21](NC(C)C)(C)C.IC>COCCOC.O.CN(C=O)C>[CH3:21][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 24758Sodium hydrideHCID 18689784(E)-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

생성물 1

HCID 18689783(E)-N-Methyl-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine수율 76.1%

시약·촉매·용매 3

HCID 962
Water
용매
2회
HCID 6228Dimethylformamide용매
HCID 80711,2-Dimethoxyethane용매2회

실험 절차

Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 rain, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil. The oil was chromatographed on silica gel (50 g), elating with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%).

후처리

  1. stirringThe mixture was stirred at ambient temperature for 3 days
  2. temperaturecooled
  3. extractionextracted with chloroform (7×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was dried under high vacuum at ambient temperature
  8. customto give a red-brown oil
  9. customThe oil was chromatographed on silica gel (50 g)
  10. concentrationconcentrated by rotary evaporation
  11. customdried under high vacuum at ambient temperature

출처 및 근거

ORD 기록
ord-4dd9d774b5cd4f7ebfe2ae7137ee96e1
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05597919

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