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Ethanol → 4-Aminopyrrolo[2,1-F][1,2,4]triazine-6-carbonitrile

HRID 1094860
ノート
印刷プレビュー

反応式

HRID 1094860 の反応式
CCO.[NH2:4][N:5]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[C:6]1[C:12]#[N:13].C(O)(=O)C.[CH:18](N)=[NH:19].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[NH2:13][C:12]1[C:6]2=[CH:7][C:8]([C:10]#[N:11])=[CH:9][N:5]2[N:4]=[CH:18][N:19]=1
参加物反応条件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 702EthanolHCID 11430Potassium CarbonateHCID 160693Formamidine acetateHCID 552958981-amino-1H-pyrrole-2,4-dicarbonitrile

生成物 1

HCID 552974584-Aminopyrrolo[2,1-F][1,2,4]triazine-6-carbonitrile収率 75.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate
溶媒

反応条件

温度
80 °C

実験手順

To a solution of EtOH (50 mL) was added 1-amino-1H-pyrrole-2,4-dicarbonitrile (1.00 g, 7.57 mmol) followed by formamidine acetate (9.46 g, 90.8 mmol) and potassium carbonate (14.6 g, 106.0 mmol). The solution was heated to 80° C. for 2 h. Upon cooling to rt, the reaction mixture was diluted with EtOAc transferred to a separatory funnel and washed with water. The organic layer was collected, dried (MgSO4), filtered, and concentrated to dryness. The crude material was then triturated with EtOH-water. The solid was collected, washed with water, and dried under vacuum to afford 0.91 g of the above compound as a yellow-orange solid (5.70 mmol, yield 75%). 1H-NMR (DMSO-d6) δ 8.37 (d, J=1.8 Hz, 1H), 8.19 (d, J=17.4, 2H), 7.93 (s, 1H), 7.27 (d, J=1.8 Hz, 1H); LCMS RT=1.14 min.

後処理

  1. temperatureUpon cooling to rt
  2. customtransferred to a separatory funnel
  3. washwashed with water
  4. customThe organic layer was collected
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material was then triturated with EtOH-water
  9. customThe solid was collected
  10. washwashed with water
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-fec8c715f39d48568b9f9f5fa8911b50
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08133995B2

反応ノート

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