Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:14]=[C:13]([NH:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:31]>CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:14]=[C:13]([N:21]([CH3:31])[CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-[4-(methylsulfonyl)phenyl]-N-tetrahydro-2H-pyran-4-yl-6-(trifluoromethyl)pyrimidin-2-amine (0.05 g) in dry dimethylformamide (2 ml) was treated with sodium hydride (0.007 g, 60% in mineral oil) and the mixture stirred at ambient temperature for 30 minutes. Iodomethane (0.01 ml) was added and the mixture stirred overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The organic layer was purified by passing through a silica bond elute column and eluting with dichloromethane. Concentration of the eluent gave the title compound as a yellow solid (0.031 g).
Workup
- stirringthe mixture stirred overnight
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
- customThe organic layer was purified
- washelute column
- washeluting with dichloromethane
Sources & evidence
- ORD record
- ord-7489cadc00124f82a4089f651da7299f
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084148B2
Linked notes
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