tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[(4-pyrimidin-5-yloxyphenyl)methylidene]propane-2-sulfinamide

HRID 1850174Notes

Reaction equation

[N:1]1[CH:6]=[C:5]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:4]=[N:3][CH:2]=1.[C:16]([S@:20]([NH2:22])=[O:21])([CH3:19])([CH3:18])[CH3:17]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:17][C:16]([S@:20](/[N:22]=[CH:12]/[C:11]1[CH:14]=[CH:15][C:8]([O:7][C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)=[CH:9][CH:10]=1)=[O:21])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 4-(pyrimidin-5-yloxy)benzaldehyde (666 mg, 3.33 mmol), (R)-(+)-tert-butanesulfinamide (450 mg, 3.71 mmol) and copper sulfate (796 mg, 4.99 mmol) in anhydrous in dichloroethane (7.648 mL) and under argon was heated at 55° C. for ˜21 hours. The reaction mixture was allowed to cool to room temperature. The slurry was filtered through a celite pad, eluted with DCM (5×10 mL). The combined filtrates were concentrated under reduced pressure and the resulting yellowish oil was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate] providing (R,E)-2-methyl-N-(4-(pyrimidin-5-yloxy)benzylidene)propane-2-sulfinamide (836 mg) as a pale viscous oil. LCMS m/z 304.0 (M+H)+, Rt 0.79 min.

Workup

temperatureto cool to room temperature
filtrationThe slurry was filtered through a celite pad
washeluted with DCM (5×10 mL)
concentrationThe combined filtrates were concentrated under reduced pressure
customthe resulting yellowish oil was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate]

Sources & evidence

ORD record: ord-445db04a21d24f5aadbbb20d6a1a69e1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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