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Dimethylformamide → 5-Mesityl-2-[(2-methoxyethyl)amino]-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598122
ノート
印刷プレビュー

反応式

HRID 598122 の反応式
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1.CN(C)C=O.[H-].[Na+].[CH3:30][O:31][CH2:32][CH2:33]Br>O>[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[C:4](=[O:21])[N:3]([CH3:22])[C:2]([NH:1][CH2:33][CH2:32][O:31][CH3:30])=[N:7][C:6]=2[N:8]([CH3:20])[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

生成物 1

HCID 589386195-Mesityl-2-[(2-methoxyethyl)amino]-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one収率 23.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (55 mg, 0.18 mmol) and N,N-dimethylformamide (2 ml) was added sodium hydride (60% in oil, 24 mg, 0.60 mmol) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 0.5 hour, to the mixture was added a solution of 2-methoxyethylbromide (232 mg, 0.60 mmol) and N,N-dimethylformamide (1 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 2 hours and heating under reflux for 2 hours, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 ml×2). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (9:1) to give 15 mg (23%) of the title compound as an oil.

後処理

  1. stirringAfter stirring at room temperature for 0.5 hour, to the mixture
  2. stirringstirred for 0.5 hour
  3. stirringAfter stirring at room temperature for 2 hours
  4. temperatureheating
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ethyl acetate (50 ml×2)
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with hexane/ethyl acetate (9:1)

出典と根拠

ORDレコード
ord-8fd1316664134612a5439380c05dce0d
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07897607B2

反応ノート

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