Methyl iodide → N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide
Reaction equation
[C:1]([C:3]1[C:4]([NH:11][C:12](=[O:14])[CH3:13])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#[N:2].[CH3:15]I.[H-].[Na+]>CS(C)=O>[C:1]([C:3]1[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#[N:2]Participants
Procedure
To a solution of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-acetamide (562 mg, 2.70 mmol) and methyl iodide (1.7 mL, 27.0 mmol) in anhydrous DMSO (14 mL) was added NaH (60% wt. dispersion in mineral oil, 130 mg, 3.23 mmol) at 0° C. The reaction mixture was stirred at RT for 16 h and was then quenched by adding water (50 mL). The resulting mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (2×100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (from 0 to >33% EtOAc/hexane in 5 min.) to afford 431 mg (72% yield) of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide as an off-white solid. MS=223 [M+1]+.
Workup
- customwas then quenched
- additionby adding water (50 mL)
- extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
- washThe combined organic layers were washed with brine (2×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by flash chromatography (from 0 to >33% EtOAc/hexane in 5 min.)
Sources & evidence
- ORD record
- ord-bff7b245a6974a6393aa42a5b22fc82d
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268840B2
Reaction notes
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