Formamidine acetate → Tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate

HRID 1616085ノート

反応式

HRID 1616085 の反応式
[NH2:1][C:2]1[C:3]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:4][S:5][C:6]=1[C:7](OCC)=[O:8].C(O)(=O)C.[CH:29](N)=[NH:30]>C(O)C>[O:8]=[C:7]1[NH:30][CH:29]=[N:1][C:2]2[C:3]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]3)=[CH:4][S:5][C:6]1=2

参加物

4

反応物 2

HCID 160693Formamidine acetateHCID 86681876Tert-butyl 4-[4-amino-5-(ethoxycarbonyl)thiophen-3-yl]piperidine-1-carboxylate

生成物 1

HCID 136359802Tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate収率 21.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

tert-Butyl 4-[4-amino-5-(ethoxycarbonyl)thiophen-3-yl]piperidine-1-carboxylate (307 mg, 0.87 mmol) was dissolved in ethanol (8 mL), and then formamidine acetate (542 mg, 5.20 mmol) was added, followed by heating under reflux for 36 hours. The reaction liquid was concentrated under a reduced pressure, and the obtained residue was dissolved in chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel chromatography (chloroform:methanol=10:1) to give tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (62.5 mg, 21.5%) as a pale yellow amorphous.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 36 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under a reduced pressure
  5. dissolutionthe obtained residue was dissolved in chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe obtained residue was purified

出典と根拠

ORDレコード
ord-1f7c8ed7417d4b6e9b6af55b9f6da7ec
出典データセット
uspto-grants-2014_07
特許番号
US08765771B2

反応ノート

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