Phosphorus oxychloride → 4-Chloro-6-(N,N-dimethylamino)-pyrido[3,4-d]pyrimidine

HRID 564760Notes

Reaction equation

HRID 564760 reaction equation
[CH3:1][N:2]([C:4]1[N:14]=[CH:13][C:7]2[N:8]=[CH:9][NH:10][C:11](=O)[C:6]=2[CH:5]=1)[CH3:3].P(Cl)(Cl)([Cl:17])=O>C(N(CC)CC)C>[Cl:17][C:11]1[C:6]2[CH:5]=[C:4]([N:2]([CH3:3])[CH3:1])[N:14]=[CH:13][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358174466-(N,N-Dimethylamino)-3H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 227274534-Chloro-6-(N,N-dimethylamino)-pyrido[3,4-d]pyrimidineYield 33%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6-(N,N-Dimethylamino)-3H-pyrido[3,4-d]pyrimidin-4-one (1.0 g, 5.25 mmol) was heated at reflux with phosphorous oxychloride (8.5 ml) and triethylamine (5.3 ml) for 3 hours. The mixture was concentrated in vacuo, azeotroping with toluene twice. The residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate (8%), the layers separated, and the aqueous extracted once more with ethyl acetate. The combined organics were washed with water and brine, dried (sodium sulphate), and concentrated in vacuo. The residue was triturated with hexane to give the product as a solid (0.36 g, 33%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroping with toluene twice
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate (8%)
  4. customthe layers separated
  5. extractionthe aqueous extracted once more with ethyl acetate
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried (sodium sulphate)
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-f0a6c0456a364414993b0ba22ebb304d
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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