Pyridine → 6-Bromo-4-chloro-2-(methylsulfanyl)quinazoline
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([S:12][CH3:13])[NH:6][C:5]2=O.N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:23]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([S:12][CH3:13])[N:6]=[C:5]2[Cl:23]Participants
4
Conditions
- Temperature
- 110 °C
Procedure
To a suspension of compound 5a (0.65 g, 2.4 mmol) in 6.2 mL of POCl3 was added 10 μL of pyridine and the mixture was heated at 110° C. for 18 hours. The reaction mixture was cooled to rt. and concentrated under reduced pressure. A saturated solution of 50 mL of aqueous NaHCO3 was added to the crude solid and the mixture was extracted with 50 mL of EtOAc. The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by chromatography on a silica gel column. Elution with n-heptane/EtOAc (4:1) as eluent afforded 11a as a white solid (0.52 g, 75%). mp: 124° C.,
Workup
- temperatureThe reaction mixture was cooled to rt
- concentrationand concentrated under reduced pressure
- additionA saturated solution of 50 mL of aqueous NaHCO3 was added to the crude solid
- extractionthe mixture was extracted with 50 mL of EtOAc
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated under reduced pressure
- custompurified by chromatography on a silica gel column
- washElution with n-heptane/EtOAc (4:1) as eluent
Sources & evidence
- ORD record
- ord-8ea4139b25434e9284733b5880cd601b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809355B2
Reaction notes
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