(5-methyl-1H-imidazol-4-yl)methyl[4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2yl]formamide → N-[(5-methyl-1H-imidazol-4-yl)methyl]-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine-2-amine
Reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([N:9](C)[C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:13]=[C:12]([C:26]([F:29])([F:28])[F:27])[N:11]=1)=O>C(O)C.Cl>[NH3:4].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][NH:9][C:10]1[N:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:13]=[C:12]([C:26]([F:29])([F:27])[F:28])[N:11]=1Participants
5
Reactant 1
Product 2
Reagents, catalysts & solvents 2
Procedure
A solution of crude (5-methyl-1H-imidazol-4-yl)methyl[4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2yl]formamide (0.27 g, 0.615 mmol) in ethanol (10 ml) and 2N hydrochloric acid (10 ml) was heated under reflux for 2 h. The solvents were then evaporated and the residue basified with 0.880 ammonia and extracted with DCM. The dried organic phase was evaporated onto silica gel and this mixture was purified on a silica gel SPE cartridge. Elution with DCM:ethanol:0.880 ammonia, 91:8:1, gave the title compound as a colourless crystalline solid (0.14 g).
Workup
- temperatureunder reflux for 2 h
- customThe solvents were then evaporated
- extractionextracted with DCM
- customThe dried organic phase was evaporated onto silica gel
- customthis mixture was purified on a silica gel SPE cartridge
- washElution with DCM
Sources & evidence
- ORD record
- ord-b954b3eeb37b487f8762052bfafbac6a
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780870B2
Reaction notes
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