Potassium Carbonate → Ethyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylate

HRID 339749ノート

反応式

HRID 339749 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[C:6]([CH3:20])[N:5]=[CH:4][N:3]=1.Cl[CH2:22][C:23]1[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:20][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:1][CH2:22][C:23]2[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=2)[C:7]=1[C:8]#[C:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 680024494-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

生成物 1

HCID 44815753Ethyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine (2.8 g), ethyl 5-chloromethyl-2-furancarboxylate (1.8 g), potassium carbonate (2.1 g) and N,N-dimethylformamide (120 ml) was heated while stirring at 70° C. for 15 hours. The mixture thus obtained was concentrated under reduced pressure. To the resultant residue, water was added. After extraction was performed with chloroform, an organic phase was dried over anhydrous sodium sulfate and then evaporated. The evaporated residue was purified by column chromatography to obtain a target substance (1 g). The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.

後処理

  1. temperaturewas heated
  2. customThe mixture thus obtained
  3. concentrationwas concentrated under reduced pressure
  4. additionTo the resultant residue, water was added
  5. extractionAfter extraction
  6. dry with materialan organic phase was dried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe evaporated residue was purified by column chromatography
  9. customto obtain a target substance (1 g)

出典と根拠

ORDレコード
ord-e228e53003564ed7bc00513b74849d0e
出典データセット
uspto-grants-2014_11
特許番号
US08895565B2

反応ノート

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