Triethylamine → (R)-2-(2-(4-chlorophenyl)piperazin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-one

HRID 1784669Notes

Reaction equation

HRID 1784669 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[C:24]1[N:29]([CH3:30])[C:28](=[O:31])[CH:27]=[C:26]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[N:25]=1.ClC1C=CNC(=O)N=1>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:15][N:14]([C:24]3[N:29]([CH3:30])[C:28](=[O:31])[CH:27]=[C:26]([C:32]4[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=4)[N:25]=3)[CH2:13][CH2:12][NH:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117377(R)-2-(4-chlorophenyl)piperazine dihydrochlorideHCID 1785178106-Chloropyrimidin-2(1H)-one

Product 1

HCID 11394925(R)-2-(2-(4-chlorophenyl)piperazin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-oneYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (R)-2-(4-chlorophenyl)piperazine dihydrochloride (1.09 g, 4.05 mmol) in tetrahydrofuran (24 ml) was added triethylamine (2.82 ml, 20.3 mmol). After stirring for 15 min at room temperature, 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (748 mg, 3.38 mmol) was added portionwise. Upon disappearance of the chloropyrimidone, the reaction mixture was condensed under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give pale yellow solid, which was recrystallized from ethanol to afford (R)-2-(2-(4-chlorophenyl)piperazin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (998 mg, 77.4%) as white crystals. The enantiomer excess was determined by HPLC (>99% ee). The crystals were converted into its dihydrochloride salt.

Workup

  1. customcondensed under reduced pressure
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give pale yellow solid, which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c5a684e1cab24b28bfa1c9f6becec9f7
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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