Diethyl Ether → HCID 118207754, compound
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Cl)[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[CH2:13]([Mg]Br)[CH3:14].CCOCC>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:13][CH3:14])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a 100 mL round-bottom flask was added 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (300 mg, 1.363 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to −78° C. Ethylmagnesium bromide in ether (3.0 M, 0.454 mL, 1.363 mmol) was added and the reaction mixture was allowed to stir for 1 hour at room temperature. LCMS indicated the reaction was complete. The reaction mixture was quenched with a few drops saturated aqueous NH4Cl and allowed to warm to room temperature. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography (ISCO 12 g, 20-100% EtOAc/hexane gradient) to give the title compound as a pasty yellow solid. ESI-MS m/z [M+H]+ calc'd for C8H8ClN3S, 214. found 214.
Workup
- customThe reaction mixture was quenched with a few drops saturated aqueous NH4Cl
- temperatureto warm to room temperature
- additionThe reaction mixture was diluted with EtOAc
- washwashed with saturated aqueous NH4Cl (3×)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe product was purified by column chromatography (ISCO 12 g, 20-100% EtOAc/hexane gradient)
Sources & evidence
- ORD record
- ord-a759e72bc5814bfb927f448d0db00076
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371321B2
Reaction notes
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