Acetone → HCID 13883924, compound

HRID 231118Notes

Reaction equation

HRID 231118 reaction equation
[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[CH:15][C:14]=2[CH3:24])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8].[CH3:25][C:26]([CH3:28])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]3[CH2:21][O:22][C:26]([CH3:28])([CH3:25])[O:23]3)=[CH:15][C:14]=2[CH3:24])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 20034500HCID 20034500, compound

Product 1

HCID 13883924HCID 13883924, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g of 5-chloro-4-{2-[4-(2,3-dihydroxypropyl)-2-methylphenoxy]ethylamino}-6-methylpyrimidine and 50 ml of acetone were dissolved in 200 ml of toluene and a small amount of p-toluenesulfonic acid was added to the solution. The mixture was then heated under reflux for 6 hours. At the end of this time, the reaction mixture was adjusted to weakly alkaline by the addition of a dilute aqueous solution of sodium hydroxide. Then the reaction mixture was washed with water and dried over anhydrous sodium sulfate. Toluene was removed by distillation under reduced pressure. The oily product thus obtained was subjected to column chromatography (Wakogel C-200, eluted with a 2:1 by volume mixture of toluene and ethyl acetate) to isolate the product and give 4.8 g of the title compound as a pale yellow oily liquid, n25.0 =1.5516.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. washThen the reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customToluene was removed by distillation under reduced pressure
  6. customThe oily product thus obtained
  7. washeluted with a 2:1 by volume mixture of toluene and ethyl acetate)
  8. customto isolate the product

Sources & evidence

ORD record
ord-e83f4175f12d4af38e86cd5644b047e3
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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