Phosphorus oxychloride → 7-Chloro-2-(methylthio)pyrido[2,3-d]pyrimidine

HRID 1826580Notes

Reaction equation

HRID 1826580 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=O)[NH:9][C:7]=2[N:8]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:10]1[CH:11]=[CH:12][C:6]2[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:8][C:7]=2[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12347632-(methylthio)pyrido(2,3-d)pyrimidin-7(8H)-one

Product 1

HCID 221346737-Chloro-2-(methylthio)pyrido[2,3-d]pyrimidine

Procedure

A suspension of 1.0 g (5.2 mmol) of 2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (Example 5) in 10 mL of phosphorus oxychloride is heated under reflux for 1 hour. The resulting solution is cooled and concentrated to give a solid, which is triturated with cold water and filtered to give 1.05 g of crude product. Recrystallization from acetonitrile lives 0.76 g (69%) of the product, mp 201-203° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe resulting solution is cooled
  4. concentrationconcentrated
  5. customto give a solid, which
  6. customis triturated with cold water
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5263f83a165b4aa3bfa7ae1d7330fd57
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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