Methyl iodide → HCID 13259338, compound

HRID 436407Notes

Reaction equation

HRID 436407 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][NH:11][C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]([CH3:24])[C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13259337HCID 13259337, compound

Product 1

HCID 13259338HCID 13259338, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 0.7 g of 1-(m-trifluoromethylphenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 10 ml of dimethylformamide was added 0.13 g of sodium hydride. To this was added a mixture of 5.1 g of methyl iodide and 5 ml of dimethylformamide, dropwise under cooling, and immediately the resulting mixture was heated for 1.5 hour in an oil bath maintained at 100° C. After the reaction was complete, the solvent was distilled off under reduced pressure to leave a residue, to which was added ice-cold water. This residue was extracted with ether, washed and dehydrated. Separation and purification were accomplished by passing the solution through a column of alumina, and the eluate obtained was concentrated to give 0.6 g of 1-(m-trifluoromethylphenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 122° - 124° C.

Workup

  1. additionTo this was added
  2. temperaturedropwise under cooling
  3. temperatureimmediately the resulting mixture was heated for 1.5 hour in an oil bath
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto leave a residue
  6. additionto which was added ice-cold water
  7. extractionThis residue was extracted with ether
  8. washwashed
  9. customSeparation and purification
  10. customthe eluate obtained
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-08cdd46589354b039ccda4d95f2348aa
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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