Dimethyl Sulfoxide → 2-[6-(Methylsulfanyl)pyrimidin-4-yl]acetonitrile

HRID 2401185Notes

Reaction equation

[C:1]([CH:3]([C:8]1[CH:13]=[C:12]([S:14][CH3:15])[N:11]=[CH:10][N:9]=1)C(OC)=O)#[N:2].[Cl-].[Na+].O.CS(C)=O>C(OCC)(=O)C>[CH3:15][S:14][C:12]1[N:11]=[CH:10][N:9]=[C:8]([CH2:3][C:1]#[N:2])[CH:13]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A microwave vial was charged with methyl cyano[6-(methylthio)-4-pyrimidinyl]acetate (Intermediate 14, 700 mg, 3.14 mmol), sodium chloride (1.0 g, 17.11 mmol), water (1 mL) and DMSO (19 mL). The mixture was stirred and heated at 160° C. for 50 minutes in the microwave. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine. The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was dissolved in DCM (10 mL) and purified by column chromatography (Biotage SP4) eluting with a gradient of 0-100% ethyl acetate and iso-hexane. Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound (292 mg) as a yellow oil;

Workup

washwashed with brine
dry with materialThe organic layer was dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in DCM (10 mL)
custompurified by column chromatography (Biotage SP4)
washeluting with a gradient of 0-100% ethyl acetate and iso-hexane
additionFractions containing the suspected product
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9c4d1a2df9434e1592e212c87a5b9899
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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