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

HRID 1526550Notes

Reaction equation

HRID 1526550 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-6c7a4e1e071b48d9854d192ec089b962
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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