Pyridine → HCID 9881337, compound

HRID 1108980Notes

Reaction equation

HRID 1108980 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[N:5]=[CH:4]1)[CH3:2].S(Cl)(Cl)=O.N1C=CC=CC=1.[CH2:21]([C:23]1[C:28]([NH2:29])=[CH:27][N:26]=[CH:25][N:24]=1)[CH3:22]>C1COCC1>[CH2:21]([C:23]1[C:28]([NH:29][C:8]([C:6]2[N:5]=[CH:4][N:3]([CH2:1][CH3:2])[CH:7]=2)=[O:10])=[CH:27][N:26]=[CH:25][N:24]=1)[CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 150474531-ethyl-1H-imidazole-4-carboxylic acidHCID 190216725-Pyrimidinamine, 4-ethyl- (9CI)

Product 1

HCID 9881337HCID 9881337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-ethyl-1H-imidazole-4-carboxylic acid (2.5 g, 17.8 mmol) and thionyl chloride (65 mL) is refluxed for 1.5 h. The thionyl chloride is removed in vacuo using toluene to azeotrope thionyl chloride. To a suspension of the residue is added THF (60 mL) and pyridine (3.2 mL, 39.2 mmol), followed by 4-ethyl-5-pyrimidineamine (2.2 g, 17.8 mmol). The reaction mixture is refluxed for 17 h, and concentrated in vacuo. The residue is taken up in water (100 mL), and the pH of the solution is adjusted to 8.0 by the addition of solid potassium carbonate. The aqueous layer is extracted with methylene chloride (3×100 mL). The organic extracts are combined, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (300 g) using 3% MeOH in CH2Cl2 as eluent. The product fractions are combined and the solvent removed. The resultant material is triturated with ether+MeOH (19+1) to give the title compound.

Workup

  1. customThe thionyl chloride is removed in vacuo
  2. additionTo a suspension of the residue
  3. temperatureThe reaction mixture is refluxed for 17 h
  4. concentrationconcentrated in vacuo
  5. additionthe pH of the solution is adjusted to 8.0 by the addition of solid potassium carbonate
  6. extractionThe aqueous layer is extracted with methylene chloride (3×100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel (300 g)
  10. customthe solvent removed
  11. customThe resultant material is triturated with ether+MeOH (19+1)

Sources & evidence

ORD record
ord-85c4b61bb74243c79bfa3a9151b63d86
Source dataset
uspto-grants-1994_06
Patent number
US05318975

Reaction notes

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