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

HRID 627611

Reaction equation

HRID 627611 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 dichloromethane, 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 dichloromethane
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fbce1ab24e0542149d7b3ac2d894b99b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Linked notes

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