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

HRID 73666
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HRID 73666 반응식
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
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참가 물질

6

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 160693Formamidine acetateHCID 552958981-amino-1H-pyrrole-2,4-dicarbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3bbf0b6a0bcf4214a110a8f25a72a24e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08829185B2

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