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

HRID 1972976
Notes
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Reaction equation

HRID 1972976 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 160693Formamidine acetateHCID 552958981-amino-1H-pyrrole-2,4-dicarbonitrile

Product 1

HCID 552974584-Aminopyrrolo[2,1-F][1,2,4]triazine-6-carbonitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a10d6009971a42ccbe0119f749c651e5
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes