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

HRID 52406

反応式

HRID 52406 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

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 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 (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), 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%).

後処理

  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. washeluting with ethyl acetate
  11. concentrationconcentrated by rotary evaporation
  12. customdried under high vacuum at ambient temperature

出典と根拠

ORDレコード
ord-cec5a6a4460948fcb08830168a7da45a
出典データセット
uspto-grants-1997_04
特許番号
US05616707

関連ノート

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