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

HRID 930451Notes

Reaction equation

HRID 930451 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-aa7383c7f17047ee8217fd130fbad691
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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