Tetrahydrofuran → HCID 22930027, compound

HRID 1295991Notes

Reaction equation

HRID 1295991 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[C:25]([C:35]#[N:36])=[N:26][C:27]([CH3:34])=[C:28]([O:31][CH2:32][CH3:33])[C:29]=1[CH3:30])=[N+]=[N-].O1CCCC1>O>[CH2:32]([O:31][C:28]1[C:29]([CH3:30])=[C:24]2[CH2:23][N:20]=[C:35]([NH2:36])[C:25]2=[N:26][C:27]=1[CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 22929849HCID 22929849, compound

Product 1

HCID 22930027HCID 22930027, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylphosphine (170 mg, 0.648 mmol) was added to a solution of the 3-(azidomethyl)-5-ethoxy-4,6-dimethyl-2-pyridinecarbonitrile (113 mg, 0.489 mmol) in a tetrahydrofuran (3 ml) —H2O (0.15 ml) mixed solvent while cooling on ice, and the mixture was stirred at room temperature for 2.5 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: ethyl acetate-methanol-29% NH3(aq)) to yield the title compound (69 mg, 69%) as a yellow solid.

Workup

  1. additionmixed solvent
  2. temperaturewhile cooling on ice
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: ethyl acetate-methanol-29% NH3(aq))

Sources & evidence

ORD record
ord-a2770345159344398201d4a67b7bc0a4
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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