Phosphorus oxychloride → 2,6-Dichloropyrido[3,2-d]pyrimidine

HRID 475330Notes

Reaction equation

HRID 475330 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([N:11]=1)=[CH:9][NH:8][C:7](=O)[N:6]=2.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:7]1[N:8]=[CH:9][C:10]2[N:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517174HCID 178517174, compound

Product 1

HCID 574611412,6-Dichloropyrido[3,2-d]pyrimidine

Procedure

6-chloro-3H-pyrido[3,2-d]pyrimidin-2-one (3.4 g, 5.2 mmol) are taken up in POCl3 (55 mL) and the mixture is heated for 3 h to 105° C. Then the reaction mixture is added dropwise to ice water, extracted with DCM, the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and 2,6-dichloro-pyrido[3,2-d]pyrimidine (HPLC-MS: MS(M+H)+=200; method AFEC) is obtained.

Workup

  1. temperaturethe mixture is heated for 3 h to 105° C
  2. extractionextracted with DCM
  3. customthe organic phase is dried on MgSO4

Sources & evidence

ORD record
ord-52b7f990777842bab11b671fdc4de15c
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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