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

HRID 1759

반응식

HRID 1759 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 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 962Water용매2회HCID 6228Dimethylformamide용매HCID 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-dimethyoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, 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 (Na2 SO4), 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), eluting 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. customdried (Na2 SO4)
  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. washeluting with ethyl acetate
  11. concentrationconcentrated by rotary evaporation
  12. customdried under high vacuum at ambient temperature

출처 및 근거

ORD 기록
ord-10d91779e086461aa563e2a37737f0b8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726316

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