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

HRID 2401185
Notes
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Reaction equation

HRID 2401185 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 59173478Methyl cyano[6-(methylthio)-4-pyrimidinyl]acetate2×

Product 1

HCID 591732732-[6-(Methylsulfanyl)pyrimidin-4-yl]acetonitrileYield 56.3%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

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

  1. washwashed with brine
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (10 mL)
  6. custompurified by column chromatography (Biotage SP4)
  7. washeluting with a gradient of 0-100% ethyl acetate and iso-hexane
  8. additionFractions containing the suspected product
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes