Potassium Carbonate → Benzyl 1-(2,6-dimethylpyrimidin-4-yl)piperidin-4-yl(methyl)carbamate
Reaction equation
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([CH3:27])[N:21]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:27][C:22]1[N:21]=[C:20]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)[CH:25]=[C:24]([CH3:26])[N:23]=1Participants
5
Procedure
A mixture of benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (17.24 mmol, 1.0 eq.), 4-chloro-2,6-dimethylpyrimidine (2.94 g, 2068 mmol, 1.2 eq.) and K2CO3 (4.76 g, 34.48 mmol, 2.0 eq.) in acetone (80 ml) was refluxed for 14 hours. The mixture was concentrated, and the residue was taken up in water (150 ml) and extracted with ethyl acetate (2×200 ml). The combined organic phases were washed with water (150 ml) and sat. NaCl solution (150 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane). Yield: 62% (3.8 g, 10.73 mmol)
Workup
- temperaturewas refluxed for 14 hours
- concentrationThe mixture was concentrated
- extractionextracted with ethyl acetate (2×200 ml)
- washThe combined organic phases were washed with water (150 ml) and sat. NaCl solution (150 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography (silica gel, 70% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ef9fa45e3d4b449eb50e458b1d2699e4
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
Loading…