Iminomethanaminium acetate → 6-Chloropyrrolo[2,1-f][1,2,4]triazin-4-amine
Reaction equation
[NH2:1][N:2]1[CH:6]=[C:5]([Cl:7])[CH:4]=[C:3]1C#N.[C:10]([O-])(=O)C.[CH:14]([NH2:16])=[NH2+:15]>CCO>[Cl:7][C:5]1[CH:4]=[C:3]2[N:2]([CH:6]=1)[N:1]=[CH:10][N:15]=[C:14]2[NH2:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred suspension of 1-amino-4-chloro-1H-pyrrole-2-carbonitrile (3.4 g, 24.02 mmol) in EtOH (160 mL) was added formamidinium acetate (25 g, 240.2 mmol). The mixture was heated to 80° C. over night. TLC analysis indicated that there was complete conversion of starting material. The reaction mixture was cooled to room temperature and then filtered. Ethanol was removed under reduced pressure and the remaining solids were purified by column chromatography (EtOAc) to afford 2.2 g of the above compound (13.1 mmol, yield 54%). 1H-NMR (MeOD-d4) δ 7.77 (s, 1H), 7.56 (d, J=1.6 Hz, 1H), 6.82 (d, J=1.6 Hz, 1H); LCMS RT=1.30 min; MS {M+H]+=168.8
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- customEthanol was removed under reduced pressure
- customthe remaining solids were purified by column chromatography (EtOAc)
Sources & evidence
- ORD record
- ord-2682426640b542699cf87a3085f59a03
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133995B2
Reaction notes
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