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

HRID 1972976
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HRID 1972976 반응식
[NH2:1][N:2]1[CH:6]=[C:5]([C:7]#[N:8])[CH:4]=[C:3]1[C:9]#[N:10].C(O)(=O)C.[CH:15](N)=[NH:16].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CCO>[NH2:10][C:9]1[C:3]2=[CH:4][C:5]([C:7]#[N:8])=[CH:6][N:2]2[N:1]=[CH:15][N:16]=1
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 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 71.4%

시약·촉매·용매 1

HCID 702Ethanol
용매

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온도
80 °C

실험 절차

1-Amino-1H-pyrrole-2,4-dicarbonitrile (3.00 g, 22.71 mmol), formamidine acetate (22.71 g, 272.47 mmol) and K2CO3 (43.93 g, 317.88 mmol) were diluted in EtOH (105 mL). The mixture was heated at 80° C. for 2 h and then cooled to rt. EtOAc (200 mL) was added and the organic layer was washed with water (100 mL), dried over MgSO4 and then concentrated to dryness. The crude material was purified by ISCO® chromatography to afford the desired product (2.58 g, 71%). 1H NMR (400 MHz, DMF-d6) δ 7.91 (s, 1H), 7.64 (s, 1H), 7.61 (s, 1H), 7.21 (s, 2H); LC-MS m/z[M+H]+ 159.9, RT 1.21 min.

후처리

  1. temperaturecooled to rt
  2. washthe organic layer was washed with water (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by ISCO® chromatography

출처 및 근거

ORD 기록
ord-a10d6009971a42ccbe0119f749c651e5
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431695B2

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