Ethanol → HCID 3078699, compound

HRID 1464305Notes

Reaction equation

HRID 1464305 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16](O)[C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][N:13]=2)[CH2:8][CH2:7]1.C(O)C.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>O>[O:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])[C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][N:13]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8021DiethylamineHCID 24813Phosphorus oxychlorideHCID 178470735HCID 178470735, compound

Product 1

HCID 3078699HCID 3078699, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (11.7 ml) was added to 3.35 g (12.5 mmoles) of ethyl 2-morpholino-4-hydroxypyrimidine-5-acetate, and the mixture was heated under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride and ice water were added. It was neutralized with sodium hydrogen carbonate. The methylene chloride layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the product were added 15 ml of ethanol and 7.0 g (95.7 mmoles) of diethylamine, and in an autoclave, the mixture was reacted at 120 ° C. for 7 hours. Water was added, and the mixture was extracted with methylene chloride. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 2.8 g (yield 56%) of the desired compound as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride and ice water
  4. additionwere added
  5. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customin an autoclave, the mixture was reacted at 120 ° C. for 7 hours
  8. extractionthe mixture was extracted with methylene chloride
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-289e38d9561744aea3042460b65af924
Source dataset
uspto-grants-1994_04
Patent number
US05304555

Reaction notes

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