Morpholine → (2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
Reaction equation
Cl[C:2]1[N:3]=[C:4]2[NH:11][C@:10]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH3:16][C@@:10]1([C:12]([F:15])([F:14])[F:13])[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=[C:2]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:3]=[C:4]2[NH:11]1Participants
3
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2.2 g of (2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one in 60 mL of morpholine is heated to 120° C. After one hour of heating and after monitoring with LC/MS, the reaction is completed. After cooling, the reaction mixture is concentrated under reduced pressure. On the obtained residue, 30 mL of cold water and 150 mL of ethyl acetate are added. The organic phase is then separated, dried on magnesium sulfate, filtered and then concentrated under reduced pressure in order to obtain 2.6 g of (2S)-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one including the following characteristics:
Workup
- temperatureAfter one hour of heating
- temperatureAfter cooling
- concentrationthe reaction mixture is concentrated under reduced pressure
- additionOn the obtained residue, 30 mL of cold water and 150 mL of ethyl acetate are added
- customThe organic phase is then separated
- customdried on magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure in order
Sources & evidence
- ORD record
- ord-6c4f23dd5f3f4b958fb89836f03e5350
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815853B2
Reaction notes
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