Water → HCID 44250837, compound

HRID 1044651Notes

Reaction equation

HRID 1044651 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.[N:31]([O-])=O.[Na+].O>C(O)(=O)C>[NH2:31][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

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 442504374,6-Dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine

Product 1

HCID 44250837HCID 44250837, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. 4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (3.0 g, 7.31 mmol) was dissolved in acetic acid (20 ml), an aqueous solution (1 ml) of sodium nitrite (605 mg, 8.78 mmol) was dripped in under water cooling, and agitation was done for 30 minutes at room temperature. After adjusting the pH to approximately 4.0 with a 2N NaOH aqueous solution, extraction was carried out 2 times using dichloromethane. After washing with water, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. The residue was dissolved in a methanol (40 ml)-ethyl acetate (40 ml) mixture solvent, 300 mg of Pd/C was added, and catalytic hydrogenation was done for 2 hours under atmospheric pressure. The Pd/C was filtered using celite, and the filtered liquid was distilled away under reduced pressure. The residue was washed with ether, and 1.63 g (52% yield) of 5-amino-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine was obtained. The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 63 are shown below.

Workup

  1. customThe synthesis method
  2. extractionwith a 2N NaOH aqueous solution, extraction
  3. washAfter washing with water
  4. customdrying
  5. distillationthe solvent was distilled away under reduced pressure
  6. dissolutionThe residue was dissolved in a methanol (40 ml)-ethyl acetate (40 ml) mixture solvent, 300 mg of Pd/C
  7. additionwas added
  8. waitcatalytic hydrogenation was done for 2 hours under atmospheric pressure
  9. filtrationThe Pd/C was filtered
  10. distillationthe filtered liquid was distilled away under reduced pressure
  11. washThe residue was washed with ether

Sources & evidence

ORD record
ord-42354e392de14dcda13a6bf5fa0189bd
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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