Ethyl Acetate → HCID 44250368, compound

HRID 1044658Notes

Reaction equation

HRID 1044658 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:15]=[C:14]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[N:13]=2)[CH2:8][CH2:7]1.[OH-].[Na+].[C:38](OCC)(=[O:40])C>CN(C)C=O>[O:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([CH:38]=[O:40])=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:15]=[C:14]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:28][CH2:29]3)[N:13]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 442504374,6-Dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine

Product 1

HCID 44250368HCID 44250368, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The synthesis method shall be explained concretely, and in order, below. Phosphorus oxychloride (0.12 ml, 1.3 mmol) was added to dimethylformamide (0.3 ml, 4.0 mmol) at 0 degrees Celsius, and this was agitated for 5 minutes at 0 degrees Celsius. To this solution, 4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine was dissolved in dimethylformamide (6 ml) and added, and this was agitated under heating for 1 hour at 100 degrees Celsius. After 2N NaOH solution was added to make the reaction liquid basic, extraction was carried out 2 times with ethyl acetate. After washing the organic layer with saturated saline, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. Purification was done by silica gel chromatography (hexane:ethyl acetate=2:3), and 350 mg of 4,6-dimorpholino-5-formyl-2-(4-phenylpiperazin-1-yl)pyrimidine (yield 80%) was obtained. The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 142 are shown below.

Workup

  1. customThe synthesis method
  2. additionadded
  3. stirringthis was agitated
  4. temperatureunder heating for 1 hour at 100 degrees Celsius
  5. customthe reaction liquid basic, extraction
  6. washAfter washing the organic layer with saturated saline
  7. customdrying
  8. distillationthe solvent was distilled away under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-4a2282d1fbea48fd9ab044da8d065330
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

Loading…