Phosphorus oxychloride → 4,6-Dichloropyrido[3,2-d]pyrimidine

HRID 1517402Notes

Reaction equation

HRID 1517402 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:10]=2[N:11]=1.C(N(CC)C(C)C)(C)C.O=P(Cl)(Cl)[Cl:24]>C1(C)C=CC=CC=1>[Cl:24][C:9]1[C:10]2[N:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 105841654,6-Dichloropyrido[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)one (3.0 g, 16.5 mmole) and N,N-diisopropylethylamine (9 ml, 50 mmole) in toluene (150 ml), was added POCl3 (4.7 ml, 50 mmol). The resulting reaction mixture was refluxed for 1.5 hour. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with cold water till pH=6-7. The organic phase was dried over MgSO4, filtrated and concentrated under reduced pressure to yield crude 4,6-dichloro-pyrido[3,2-d]pyrimidine which was not purified but used as such for further reactions.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 1.5 hour
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  5. washwashed with cold water till pH=6-7
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef689e445a5e43a58a70e19a7010b276
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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