Dimethylamine → HCID 58320442, compound

HRID 1044650Notes

Reaction equation

HRID 1044650 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[N:6]=1.O>O1CCCC1>[Cl:11][C:9]1[CH:10]=[C:5]([N:2]([CH3:3])[CH3:1])[N:6]=[C:7]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[N:8]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 58320457HCID 58320457, compound

Product 1

HCID 58320442HCID 58320442, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The synthesis method shall be explained concretely following the order below. 50% dimethylamine aqueous solution (2.9 ml) was added to a solution of 4,6-dichloro-2-(4-phenylpiperazin-1-yl)pyrimidine (1.01 g, 3.26 mmol) in tetrahydrofuran (10 ml) solution, and this was agitated overnight at room temperature. Water was added and extraction was carried out 2 times with ethyl acetate. After washing the organic layer in saturated saline, drying was done with MgSO4, the solvent was distilled away under reduced pressure, and a 4-chloro-6-dimethylamino-2-(4-phenylpiperazin-1-yl)pyrimidine powder was obtained. This powder was used in the next reaction without separation and refinement. Morpholine (6.0 ml) was added to this powder, and this was agitated at 100 degrees Celsius overnight. After cooling, water was added and extraction was carried out 2 times with dichloromethane. The organic layer was washed with saturated saline, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. The residue was washed with ether, and 810 mg (two step yield: 70%) of coarse crystals of 6-dimethylamino-4-morpholino-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 2 are shown below.

Workup

  1. customThe synthesis method
  2. extractionextraction
  3. washAfter washing the organic layer in saturated saline
  4. customdrying
  5. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b47aac8dcb8440fdbc6aa0733ce2a664
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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