Hydrochloric Acid → HCID 53628942, compound

HRID 1784677Notes

Reaction equation

HRID 1784677 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][C:11]([CH3:16])([CH3:15])[NH:10]2)=[CH:5][CH:4]=1.[Cl:17][C:18]1[N:23]([CH3:24])[C:22](=[O:25])[CH:21]=[C:20]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:19]=1.C(N(CC)CC)C.Cl.C(OCC)(=O)C>O1CCCC1>[ClH:2].[ClH:17].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][N:13]([C:18]3[N:23]([CH3:24])[C:22](=[O:25])[CH:21]=[C:20]([C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)[N:19]=3)[CH2:12][C:11]([CH3:16])([CH3:15])[NH:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117387HCID 67117387, compound

Product 1

HCID 53628942HCID 53628942, compoundYield 187.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-chlorophenyl)-6,6-dimethyl-piperazine hydrochloride (155 mg, 0.52 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (111 mg, 0.50 mmol) and triethylamine (0.42 mL, 2.50 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 6 h. The whole was evaporated in vacuo and the residue was extracted with dichloromethane. The organic layer was washed with water, dried and concentrated in vacuo. The residue was dissolved in methanol (5 mL) and treated with 4M hydrogen chloride in ethyl acetate (0.50 mL, 2.0 mmol) for 20 min. After removing the solvent, filtrating and washing the precipitate with ethanol gave 2-(2-(4-chlorophenyl)-6,6-dimethyl-piperazin-4-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one dihydrochloride (235 mg, 97%).

Workup

  1. customThe whole was evaporated in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in methanol (5 mL)
  7. customAfter removing the solvent
  8. filtrationfiltrating
  9. washwashing the precipitate with ethanol

Sources & evidence

ORD record
ord-4b6569ce1e9846a4b5c75f5aa63335d8
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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