Phosphorus oxychloride → 5-Bromo-4-chloro-6-methylthieno[2,3-d]pyrimidine
Reaction equation
[Br:1][C:2]1[C:10]2[C:9](O)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[CH3:12].O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[C:10]2[C:9]([Cl:15])=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[CH3:12]Participants
3
Conditions
- Temperature
- 110 °C
Procedure
To a 25-mL round-bottom flask containing 5-bromo-6-methylthieno[2,3-d]pyrimidin-4-ol (100 mg, 0.41 mmol, 1.00 equiv) in POCl3 (10 mL) was stirred for 1 h at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was then quenched with saturated aqueous sodium carbonate, extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. After concentrated under vacuum, this resulted 5-bromo-4-chloro-6-methylthieno[2,3-d]pyrimidine (79 mg, 73%) as a yellow solid.
Workup
- concentration