2,6-Lutidine → HCID 57561157, compound

HRID 1724856Notes

Reaction equation

HRID 1724856 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6](O)[C:7]2[C:8]([N:23]=1)=[N:9][C:10]([C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:11][N:12]=2.O=P(Cl)(Cl)[Cl:27].N1C(C)=CC=CC=1C>C(Cl)(Cl)Cl>[Cl:27][C:6]1[C:7]2[C:8](=[N:9][C:10]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:11][N:12]=2)[N:23]=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178494543HCID 178494543, compound

Product 1

HCID 57561157HCID 57561157, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Methoxymethyl-3-(3-trifluoromethyl-pyridin-2-yl)-pyrido-[2,3-b]pyrazin-8-ol (146 mg, 0.436 mmol) is dissolved in a solution of CHCl3 (20 mL), POCl3 (0.12 ml, 1.31 mmol) and 2,6-lutidine (0.2 mL, 1.31 mmol). The mixture is heated at reflux overnight. The reaction is concentrated under reduced pressure. EtOAc (30 mL) is added and the mixture is extracted with NaHCO3 (aq) (30 mL) and brine (30 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure. The crude product is purified by silica gel preparatory TLC eluting with hexanes/EtOAc (1:1) to yield the title compound as a light yellow oil that solidifies upon standing.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction is concentrated under reduced pressure
  4. additionEtOAc (30 mL) is added
  5. extractionthe mixture is extracted with NaHCO3 (aq) (30 mL) and brine (30 mL)
  6. extractionThe organic extract
  7. dry with materialis dried over Na2SO4
  8. customthe solvent removed under reduced pressure
  9. customThe crude product is purified by silica gel preparatory TLC
  10. washeluting with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-ff73410ea3af447eb31848b84e9ea520
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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