Benzaldehyde → 2-phenyl-6-(pyridin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2363925ノート

反応式

HRID 2363925 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.C(=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>CC(O)=O>[C:17]1([CH:27]2[NH:1][C:2]3[CH:6]=[C:5]([C:7]4[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=4)[S:4][C:3]=3[C:13](=[O:14])[NH:15]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

生成物 1

HCID 667432022-phenyl-6-(pyridin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one収率 28.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (99.9 mg, 0.456 mmol), p-toluenesulfonic acid monohydrate (8.67 mg, 0.046 mmol), benzaldehyde (0.056 mL, 0.547 mmol) and toluene (5 mL) was refluxed for 2 h. The reaction didn't occur. After cooling, AcOH (3 mL) was added, and the mixture was refluxed for 3 h. The reaction mixture was concentrated in vacuo. The residue was suspended in DMSO (3 mL) and the insoluble materials were filtered off. The filtrate was purified by preparative HPLC (ODS column, 0.1% TFA, water-MeCN=95:5-0:100). The fractions containing the object were basified by sat. aqueous sodium hydrogen carbonate, and the organic materials were extracted with EtOAc. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the title compound (4.0 mg, yield 2.86%) as a yellow solid:

後処理

  1. temperaturewas refluxed for 2 h
  2. customThe reaction
  3. temperatureAfter cooling
  4. temperaturethe mixture was refluxed for 3 h
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. filtrationthe insoluble materials were filtered off
  7. customThe filtrate was purified by preparative HPLC (ODS column, 0.1% TFA, water-MeCN=95:5-0:100)
  8. additionThe fractions containing the object
  9. extractionthe organic materials were extracted with EtOAc
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0c66a374bf1640fd8a091294cea40fd9
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

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