Water → 5-Chloro-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine

HRID 1044654Notes

Reaction equation

HRID 1044654 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[N:8]=2)[CH2:3][CH2:2]1.[Cl:31]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:31][C:12]1[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:8][C:9]([N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)=[N:10][C:11]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 442504374,6-Dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine

Product 1

HCID 442513235-Chloro-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidineYield 46%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. 4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (300 mg, 0.73 mmol) was dissolved in chloroform solution (5 ml), benzoyl peroxide (0.3 mg, 0.0014 mmol) and N-chlorosuccinimide (117 mg, 0.87 mmol) was added, and refluxed under heating for 1 hour. Water was added, and extraction was done with dichloromethane. 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=4:1), and 142 mg of 5-chloro-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine was obtained (yield 46%). The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 130 are shown below.

Workup

  1. customThe synthesis method
  2. temperaturerefluxed
  3. temperatureunder heating for 1 hour
  4. extractionextraction
  5. washAfter washing the organic layer with saturated saline
  6. customdrying
  7. distillationthe solvent was distilled away under reduced pressure
  8. customPurification

Sources & evidence

ORD record
ord-3d3ce296a70b40cfa29cb59e45f92637
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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