Water → HCID 19981121, compound

HRID 1460905Notes

Reaction equation

HRID 1460905 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:13])[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)=O.[CH2:14](I)[CH3:15].[OH2:17]>CN(C)C=O>[CH3:3][C:4]([CH3:13])([CH2:14][CH3:15])[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13645651HCID 13645651, compound

Product 1

HCID 19981121HCID 19981121, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of oil-free sodium hydride (2.4g, 0.1 moles) in dry dimethylformamide (60 mls) was added dropwise a solution of 2-methyl-1-(pyrimid-5-yl)-propan- 1-one in dry dimethylformamide (20 mls). The temperature rose to 35° C. and effervescence was observed. After the addition was complete, the mixture was stirred at room temperature for twenty minutes, and a solution of ethyl iodide (18.72 g, 0.12 moles) in dry dimethylformamide was added with external cooling provided by a water bath. The resulting mixture was stirred at room temperature for three hours, left to stand overnight and then poured into water and extracted twice with ether. The combined ether extracts were washed with water and dried over magnesium sulphate. After filtration, the solvent was removed in vacuo to give an oil. Distillation at reduced pressure (70°-82° C. at 0.3 mm of mercury) gave an oil (8.4 g) which was used without further purification. NMR analysis indicated that, in addition to the desired intermediate, the product contained 1-(O-ethyl)-1-(pyrimid-5-yl)-2-methylprop-1-ene. This latter by-product did not adversely affect the course of the second stage of the reaction.

Workup

  1. customrose to 35° C.
  2. additionAfter the addition
  3. temperaturewith external cooling
  4. customprovided by a water bath
  5. stirringThe resulting mixture was stirred at room temperature for three hours
  6. waitleft
  7. extractionextracted twice with ether
  8. washThe combined ether extracts were washed with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationAfter filtration
  11. customthe solvent was removed in vacuo
  12. customto give an oil
  13. distillationDistillation at reduced pressure (70°-82° C. at 0.3 mm of mercury)

Sources & evidence

ORD record
ord-efc312ee554a4b0296aaeb88033c4df4
Source dataset
uspto-grants-1991_12
Patent number
US05073187

Reaction notes

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