Triphenylphosphine → HCID 18350690, compound

HRID 430517Notes

Reaction equation

HRID 430517 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:16]([NH:17][C:18](=O)[CH3:19])=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C1C=CN=CC=1.O1CCOCC1>[CH3:19][C:18]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9](=[O:10])[C:11]2[C:16](=[N:15][CH:14]=[CH:13][N:12]=2)[N:17]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54476299HCID 54476299, compound

Product 1

HCID 18350690HCID 18350690, compound

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of 3-acetamidopyrazine-2-carboxylic acid 2-chlorophenylamide (0.816 g, 2.81 mmol), triphenylphosphine (2.21 g, 8.43 mmol), and 4-dimethylaminopyridine (0.034 g, 0.28 mmol) in dioxane (35 mL) was added diethyl azodicarboxylate (1.33 mL, 8.43 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 (1.5×5 inches, packed in hexane) with elution proceeding as follows: 20% ethyl acetate/hexane (250 mL), forerun; 40% ethyl acetate/hexane (1600 mL), unweighed triphenylphosphine oxide; 60% ethyl acetate/hexane (500 mL) and 75% ethyl acetate/hexane (500 mL), nil; 80% ethyl acetate/hexane (1000 mL), 0.62 g (81%) of 2-methyl-3-(2-chloro-phenyl)-3H-pteridin-4-one as a brown foam which was suitable for use without further purification. A sample was triturated with hexane.

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 (1.5×5 inches, packed in hexane) with elution proceeding
  9. custom80% ethyl acetate/hexane (1000 mL), 0.62 g (81%) of 2-methyl-3-(2-chloro-phenyl)-3H-pteridin-4-one as a brown foam which was suitable for use without further purification
  10. customA sample was triturated with hexane

Sources & evidence

ORD record
ord-d55d690d501041e7977cfd47e3e0d514
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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