Sodium Hydroxide → (2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one
Reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:8]=[C:9]2[NH:16][C@:15]([CH3:21])([C:17]([F:20])([F:19])[F:18])[CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1.[OH-].[Na+]>ClCCCl.O.C(OCC)(=O)C>[Cl:3][C:7]1[N:8]=[C:9]2[NH:16][C@:15]([CH3:21])([C:17]([F:20])([F:19])[F:18])[CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
41.60 mL (446.50 mmol) of phosphorus oxychloride are added, at room temperature and under an argon atmosphere, to a suspension of 35 g (148.80 mmol) of (S)-7-hydroxy-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one in 350 mL of 1,2-dichloroethane. The resulting mixture is then heated at 70° C. for 4 hours. After cooling, the reaction mixture is evaporated to dryness under vacuum. The residue obtained is taken up in 35 mL of cold water and 500 mL of ethyl acetate. 32% sodium hydroxide is added to the mixture obtained, to pH=6-7. The organic phase is then separated out and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 20 g of (S)-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one, the characteristics of which are as follows:
Workup
- temperatureAfter cooling
- customthe reaction mixture is evaporated to dryness under vacuum
- customThe residue obtained
- customobtained, to pH=6-7
- customThe organic phase is then separated out
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-709d5c575cdd4029a65765bd9d5f7af6
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321790B2
Reaction notes
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