Phosphorus oxychloride → 4-((4-Chloro-5-iodopyrimidin-2-yl)amino)benzonitrile
Reaction equation
O[C:2]1[C:7]([I:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=O)=[CH:12][CH:11]=2)[N:3]=1.P(Cl)(Cl)([Cl:21])=O>C(OCC)(=O)C>[Cl:21][C:2]1[C:7]([I:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]#[N:16])=[CH:12][CH:11]=2)[N:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To 4-((4-hydroxy-5-iodopyrimidin-2-yl)amino)benzamide (J11, 1.35 g), phosphorus oxychloride (14 mL) was added at room temperature, and the mixture was stirred at 90° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then poured into ice, and then ethyl acetate was added to the mixture. The organic layer was separated, washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid matter was washed with a mixed solvent of diisopropyl ether and chloroform, and then dried under reduced pressure to obtain 4-((4-chloro-5-iodopyrimidin-2-yl)amino)benzonitrile (J12, 764 mg) as pale yellow solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- additionpoured into ice
- customThe organic layer was separated
- washwashed successively with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- washThe obtained solid matter was washed with a mixed solvent of diisopropyl ether and chloroform
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-fca696d3241647fa8174938fe8d92496
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145415B2
Reaction notes
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