Iodoethane → HCID 9856111, compound

HRID 2300072Notes

Reaction equation

HRID 2300072 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:15](=[O:16])[NH:14][C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=1.I[CH2:18][CH3:19]>CN(C)C=O>[CH2:18]([N:14]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([CH3:3])[C:15]1=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 9964420HCID 9964420, compound

Product 1

HCID 9856111HCID 9856111, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of NaH (261 mg of a 60% suspension of NaH in mineral oil) in 40 mL of dimethylformamide was added 6-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (926 mg, 4.48 mmol). The reaction mixture was heated to 50° C. resulting in a clear solution. The solution was cooled slightly, and iodoethane (491 μL, 6.14 mmol) was added. The reaction was heated at 50° C. for 10 minutes, then cooled to room temperature and partitioned between ice water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was partitioned between hexane and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Hexane was added and the resultant solid collected by filtration to provide 824 mg (78%) of 8-ethyl-6-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 84-86° C.

Workup

  1. customresulting in a clear solution
  2. temperatureThe solution was cooled slightly
  3. temperatureThe reaction was heated at 50° C. for 10 minutes
  4. temperaturecooled to room temperature
  5. custompartitioned between ice water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was partitioned between hexane and water
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. additionHexane was added
  14. filtrationthe resultant solid collected by filtration

Sources & evidence

ORD record
ord-fa4f5e26237d4e958c13cf755ae0c186
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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