Phosphorus oxychloride → 2,5-Dichloropyrido[3,4-b]pyrazine

HRID 930444

Reaction equation

HRID 930444 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][C:10](=O)[NH:11][C:6]=2[CH:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]2=[N:8][CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 867157425-Chloropyrido[3,4-b]pyrazin-2(1H)-one

Product 1

HCID 867157432,5-Dichloropyrido[3,4-b]pyrazineYield 92.4%

Conditions

Temperature
110 °C

Procedure

A suspension of 5-chloropyrido[3,4-b]pyrazin-2(1H)-one (0.57 g, 3.14 mmol) in phosphorus oxychloride (10.24 mL, 110 mmol) was stirred at 110° C. for two hours, and then concentrated. The residue was dissolved in DCM, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound (580 mg, 2.90 mmol). MS m/z=200 (M+H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cadff68031f84708a62f698751562d34
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Linked notes

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