Ethanol → HCID 13079790, compound

HRID 1284090Notes

Reaction equation

HRID 1284090 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=O.C(O)C.[NH2:21][C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(OC(C)C)(C)C>C(OCC)(=O)C>[N:21]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=2)=[CH:2][N:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]=12

Participants

6

Reactant 4

HCID 702EthanolHCID 7914Diisopropyl EtherHCID 79782-AminopyrimidineHCID 12399237HCID 12399237, compound

Product 1

HCID 13079790HCID 13079790, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 25.5 g of ethyl 2-[4-(chloroacetyl)phenyl]propionate, 50 ml of ethanol and 19 g of 2-aminopyrimidine is heated under reflux for 3 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The mixture is extracted with ethyl acetate, and the extract is washed with water, dried and concentrated to give a reddish brown oil. To the oil are added ethyl acetate and isopropyl ether, and the crystalline precipitate is filtered off and recrystallized from ethanol to give 8.4 g of ethyl 2-[4-(imidazo[1,2-a]pyrimidin-2-yl)phenyl]propionate as colorless scales melting at 171°-173°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe ethanol is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give a reddish brown oil
  10. filtrationthe crystalline precipitate is filtered off
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3241812738164dbcb2fa92fcbee681fe
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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