Hydrogen Peroxide → HCID 71237062, compound

HRID 2280821Notes

Reaction equation

HRID 2280821 reaction equation
[CH2:1]([C:3]1([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:2].[OH:19]O.[OH-].[Na+]>CS(C)=O.O>[CH2:1]([C:3]1([NH:8][C:9]2[C:14]([C:15]([NH2:16])=[O:19])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 71237256HCID 71237256, compound

Product 1

HCID 71237062HCID 71237062, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-(1-ethylcyclopentylamino)-2-(methylthio)-pyrimidine-5-carbonitrile (830 mg, 3.2 mmol) in DMSO (10 mL) was added aqueous hydrogen peroxide (1.8 g, 30%, 16 mmol), and aqueous sodium hydroxide solution (2.7 mL, 6 mol/L, 16 mmol) at 0° C. The mixture was stirred at 50° C. for 15 min and diluted with water. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under reduced pressure gave the crude product, which was purified by silica gel column chromatography (5% methanol in DCM) to afford the desired product as a white solid (800 mg, 2.9 mmol, 90% yield). MS (ESI) m/z=281.2 [M+1]

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationConcentration under reduced pressure
  6. customgave the crude product, which
  7. customwas purified by silica gel column chromatography (5% methanol in DCM)

Sources & evidence

ORD record
ord-12a3797f1d08415da64a782af96ba1d9
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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