Triphenylphosphine → 4(3H)-Pteridinone, 2-methyl-3-(o-tolyl)-

HRID 430515Notes

Reaction equation

HRID 430515 reaction equation
[C:1]1(C)[C:2]([C:7](N)=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:11]([NH:14][C:15]1[C:16]([C:21]([OH:23])=O)=[N:17][CH:18]=[CH:19][N:20]=1)(=O)[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:43](C(OCC)=O)=NC(OCC)=O>CN(C)C1C=CN=CC=1.O1CCOCC1>[CH3:12][C:11]1[N:43]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:7])[C:21](=[O:23])[C:16]2[C:15](=[N:20][CH:19]=[CH:18][N:17]=2)[N:14]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 697097723-Acetamidopyrazine-2-carboxylic acid o-toluamide

Product 1

HCID 2107974(3H)-Pteridinone, 2-methyl-3-(o-tolyl)-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3-acetamidopyrazine-2-carboxylic acid o-toluamide (1.0 g, 3.70 mmol), triphenylphosphine (2.91 g, 11.1 mmol), and 4-dimethylaminopyridine (0.045 g, about 10 mol %) in dioxane (45 mL) was added diethyl azodicarboxylate (1.75 mL, 11.1 mmol) dropwise via syringe. The reaction was refluxed overnight, cooled to ambient temperature and concentrated. The residue was partitioned between methylene chloride and water. The phases were separated and the organic layer was washed with brine, dried and concentrated. The residue was flash chromatographed on silica gel (2.25×4 inches, packed in hexane) with elution proceeding as follows: 20%-80% ethyl acetate/hexane, forerun; 85% ethyl acetate/hexane (1000 mL), 0.71 g (76%) of 2-methyl-3-(2-methyl-phenyl)-3H-pteridin-4-one which was suitable for use without further purification. A sample was recrystallized from ethyl acetate.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe phases were separated
  5. washthe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed on silica gel (2.25×4 inches, packed in hexane) with elution proceeding
  9. custom85% ethyl acetate/hexane (1000 mL), 0.71 g (76%) of 2-methyl-3-(2-methyl-phenyl)-3H-pteridin-4-one which was suitable for use without further purification
  10. customA sample was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2ee21091907241e0a50e9d23bb778afc
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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