Isobutyl iodide → 6-Chloro-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 1181673

Reaction equation

HRID 1181673 reaction equation
I[CH2:2][CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[NH:18][C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=1>CN(C)C=O.Cl>[Cl:12][C:13]1[N:18]([CH2:2][CH:3]([CH3:5])[CH3:4])[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=1

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 961416-chloro-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 52825666-Chloro-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dioneYield 55.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-Iodo-2-methylpropane (4.6 g) and potassium carbonate (8.62 g) were added to a solution of 6-Chloro-3-methylpyrimidine-2,4[1H,3H]-dione (2.0 g) in dimethylformamide (10 ml). The mixture was heated at 90° C. for 18 hours then cooled to room temperature. The solution was diluted with 5% aqueous HCl solution until solution becomes acidic and extracted twice with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexanes: ethyl acetate (1:1) to give the subtitle compound (1.5 g).

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with hexanes: ethyl acetate (1:1)

Sources & evidence

ORD record
ord-4514b9862d8d4d7ba611934968b7743e
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Linked notes

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