Methyl iodide → HCID 135788279, compound

HRID 1822784Notes

Reaction equation

HRID 1822784 reaction equation
[CH:1]1([O:7][CH2:8][C:9]2[NH:14][C:13](=[S:15])[NH:12][C:11](=[O:16])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.IC.[C:19](=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([O:7][CH2:8][C:9]2[N:14]=[C:13]([S:15][CH3:19])[NH:12][C:11](=[O:16])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22170065HCID 22170065, compound

Product 1

HCID 135788279HCID 135788279, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-cyclohexyloxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.2 g), toluene (5.5 mL), iodomethane (0.48 g) and potassium carbonate (0.57 g) was heated at 90° C. in a sealed tube for 16 h. The mixture was partitioned in water and ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography (40% ethyl acetate in hexanes) to afford 6-cyclohexyloxymethyl-2-methylsulfanyl-3H-pyrimidin-4-one (90 mg).

Workup

  1. customThe mixture was partitioned in water
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9770a3050551434f895ec82356a09f49
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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