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

HRID 627616Notes

Reaction equation

HRID 627616 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-1805bba726ee48d7972ee23fce99471d
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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