Piperidine → N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

HRID 337728

反応式

HRID 337728 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH:12]=O.N1CCCCC1.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH2:12][NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 8082PiperidineHCID 689584-AminopyrimidineHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine収率 52.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 4-aminopyrimidine (20.0 g, 210 mmol), 2,4-dimethoxybenzaldehyde (69.9 g, 421 mmol) and piperidine (2.08 mL, 21.0 mmol) in toluene (1 L) was stirred for 7 hours under reflux, and the solvent was subjected to azeotropic distillation with water. After allowing to cool, the reaction solution was diluted with ethanol (500 mL). Sodium borohydride (7.96 g, 210 mmol) was added thereto with cooling on ice, and the mixture was stirred at room temperature for 16 hours. To the reaction solution, water (500 mL) was added, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate/methanol=95:5) to yield the title compound (27.0 g, 52%) as a colorless solid.

後処理

  1. temperatureunder reflux
  2. distillationthe solvent was subjected to azeotropic distillation with water
  3. temperatureto cool
  4. additionthe reaction solution was diluted with ethanol (500 mL)
  5. temperaturewith cooling on ice
  6. extractionan organic layer was extracted
  7. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  8. concentrationAfter vacuum concentration
  9. customthe residue was purified with silica gel chromatography (ethyl acetate/methanol=95:5)

出典と根拠

ORDレコード
ord-9da8027bd5b44ede81a610d6f916a157
出典データセット
uspto-grants-2014_11
特許番号
US08889741B2

関連ノート

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