Ytterbium triflate → HCID 86613870, compound

HRID 2246460Notes

Reaction equation

HRID 2246460 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[NH2:26][C:27]1[C:28]([C:37]#[N:38])=[N:29][C:30]([Cl:36])=[C:31](N)[C:32]=1CC>C(OCC)(OCC)OCC>[Cl:36][C:30]1[N:29]=[C:28]([C:37]#[N:38])[C:27]2[N:26]=[CH:28][N:29]([CH2:30][CH3:31])[C:32]=2[CH:31]=1

Participants

4

Reactant 2

HCID 2733225Ytterbium triflateHCID 87541755HCID 87541755, compound

Product 1

HCID 86613870HCID 86613870, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

Ytterbium triflate (75 mg) was added to a solution of 3-amino-6-chloro-4-ethyl-amino-pyridine-2-carbonitrile (1.41 g) in triethyl orthoformate (50 mL). The mixture was heated at 120° C. under stirring for 2.5 hours, than concentrated under reduced pressure. The residue was chromatographed (eluent: dichloromethane/ethyl acetate 9/1) to yield a solid which was triturated with diethyl ether and filtered off to afford the title compound (0.973 g, 66%) as white crystals (mp=138° C.). 1H NMR (CDCl3) δ: 8.17 (s, 1H); 7.62 (s, 1H); 4.31 (q, J=8 Hz, 2H); 1.62 (t, J=8 Hz, 3H). 13C NMR (CDCl3) δ: 147.5, 143.8, 142.9, 141.7, 124.0, 114.1, 109.2, 40.9, 15.2.

Workup

  1. concentrationthan concentrated under reduced pressure
  2. customThe residue was chromatographed (eluent: dichloromethane/ethyl acetate 9/1)
  3. customto yield a solid which
  4. customwas triturated with diethyl ether
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-bd48475c4b8f44f8a5b8166fc2e66151
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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