Phosphorus oxychloride → 4,7-Dichloropyrido[3,2-d]pyrimidine

HRID 1526558Notes

Reaction equation

HRID 1526558 reaction equation
[Cl:1][C:2]1[CH:11]=[N:10][C:9]2[C:8](=O)[N:7]=[CH:6][NH:5][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.P(Cl)(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][C:8]1[C:9]2[N:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1785182197-chloro-1H-pyrido[3,2-d]pyrimidin-4-one

Product 1

HCID 714284454,7-Dichloropyrido[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 7-chloropyrido[3,2-d]pyrimidin-4(1H)-one (250 mg, 1.377 mmol) in toluene (12 mL) were added DIPEA (0.73 mL, 4.20 mmol) and phosphorus oxychloride (0.391 mL, 4.27 mmol), and the reaction was stirred at reflux for 1 hour. After cooling to RT, the reaction mixture was concentrated to provide the title compound. LC/MS (ESI+) m/z=200 (M+H)+.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e0b1df88ef4e49cb9c77cec41a178fc8
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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