(NZ)-2-methyl-N-[[2-(trifluoromethyl)pyrimidin-5-yl]methylidene]propane-2-sulfinamide → 2-Methyl-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}propane-2-sulfinamide
Reaction equation
[CH3:1][C:2]([S:5](/[N:7]=[CH:8]\[C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][CH:14]=1)=[O:6])([CH3:4])[CH3:3].[CH3:19][Li]>C1(C)C=CC=CC=1>[CH3:4][C:2]([S:5]([NH:7][C@@H:8]([C:9]1[CH:14]=[N:13][C:12]([C:15]([F:18])([F:17])[F:16])=[N:11][CH:10]=1)[CH3:19])=[O:6])([CH3:1])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 2-methyl-N-{(1Z)-[2-(trifluoromethyl)pyrimidin-5-yl]methylene}propane-2-sulfinamide (14.3 g, 51.2 mmol) in toluene (260 mL) at −70° C. was added methyllithium (1.6 M; 35.0 mL, 56.0 mmol). The mixture was stirred at −70° C. for 15 min. The mixture was quenched with sat. NH4Cl and the reaction was allowed to warm to ambient temperature. The mixture was extracted with dichloromethane (3×). The combined organic extracts was dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→35% hexanes/ethyl acetate then 100% ethyl acetate→94% ethyl acetate/methanol) gave the title compound (7.23 g). MS 240.0 [(M+1)-56].
Workup
- customThe mixture was quenched with sat. NH4Cl
- temperatureto warm to ambient temperature
- extractionThe mixture was extracted with dichloromethane (3×)
- dry with materialThe combined organic extracts was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by silica gel chromatography (100% hexanes
Sources & evidence
- ORD record
- ord-663255b2c332423cbed30acc4a9345d1
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238647B2
Reaction notes
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