Phosphorus oxychloride → 7-Chloro-2-(methylthio)pyrido[2,3-d]pyrimidine
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]=1Participants
3
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
- temperatureis heated
- temperatureunder reflux for 1 hour
- temperatureThe resulting solution is cooled
- concentrationconcentrated
- customto give a solid, which
- customis triturated with cold water
- filtrationfiltered
Sources & evidence
- ORD record
- ord-5263f83a165b4aa3bfa7ae1d7330fd57
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053070B2
Reaction notes
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