Morpholine → 5-Chloro-4-{2-[4-(2-morpholinoethyl)-2-methylphenoxy]ethylamino}-6-methylpyrimidine

HRID 231120Notes

Reaction equation

HRID 231120 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][NH:11][C:12]2[C:17]([Cl:18])=[C:16]([CH3:19])[N:15]=[CH:14][N:13]=2)=[C:6]([CH3:22])[CH:5]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(O)C>[Cl:18][C:17]1[C:12]([NH:11][CH2:10][CH2:9][O:8][C:7]2[CH:20]=[CH:21][C:4]([CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:5][C:6]=2[CH3:22])=[N:13][CH:14]=[N:15][C:16]=1[CH3:19]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 200345054-{2-[4-(2-Bromoethyl)-2-methylphenoxy]ethylamino}-5-chloro-6-methylpyrimidine

Product 1

HCID 138839155-Chloro-4-{2-[4-(2-morpholinoethyl)-2-methylphenoxy]ethylamino}-6-methylpyrimidineYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.0 g of 4-{2-[4-(2-bromoethyl)-2-methylphenoxy]ethylamino}-5-chloro-6-methylpyrimidine and 1.4 g of morpholine were dissolved in 40 ml of ethanol, and the mixture was charged into an autoclave. Then, the mixture was allowed to react at 120° to 130° C. for 8 hours. At the end of this time, the ethanol was removed by distillation and water was added to the residue. The oily substance which separated was then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the ethyl acetate was removed by distillation under reduced pressure to obtain an oily substance. The substance obtained was subjected to column chromatography (Wakogel C-200, eluted with ethanol), to obtain 2.6 g of the title compound as a pale yellow oily liquid, n25.7 =1.5643.

Workup

  1. additionthe mixture was charged into an autoclave
  2. customto react at 120° to 130° C. for 8 hours
  3. customAt the end of this time, the ethanol was removed by distillation and water
  4. additionwas added to the residue
  5. customThe oily substance which separated
  6. extractionwas then extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customafter which the ethyl acetate was removed by distillation under reduced pressure
  10. customto obtain an oily substance
  11. customThe substance obtained
  12. washwas subjected to column chromatography (Wakogel C-200, eluted with ethanol)

Sources & evidence

ORD record
ord-d2b2ca943ed94db0a9d3850b10e2991d
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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