Water → 2-tert-Butyl-4-{4-[3-(4-methyl-5-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-tert-butyl-pyrimidine hydrochloride

HRID 896221Notes

Reaction equation

HRID 896221 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][Cl:20])[CH2:13][CH2:12]2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[C:30]([CH3:31])=[N:29][N:28]=[C:27]1[SH:32].[I-].[K+].O>CN(C)C=O.C(OCC)(=O)C>[ClH:20].[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][S:32][C:27]3[N:26]([CH3:25])[C:30]([CH3:31])=[N:29][N:28]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 223498712-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-tert-butyl-pyrimidineHCID 178434152HCID 178434152, compound

Product 1

HCID 116702232-tert-Butyl-4-{4-[3-(4-methyl-5-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-tert-butyl-pyrimidine hydrochlorideYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-tert-butyl-pyrimidine (2.83 mmol), 0.4 g of 4-Methyl-5-methyl-4H-[1,2,4]triazole-3-thiol (3.09 mmol), 0.2 g of lithium-hydroxide (8.35 mmol) and a spatula tip of potassium iodide werde stirred in 20 ml of dimethylformamide for 2 h at 80° C. After addition of water and ethyl acetate, the organic phase was separated and dried over magnesium sulfate. After filtration and evaporation of the solvent, the crude product was purified by column chromatography on silica gel using dichloromethane-methanol (1-6%). Fractions containing the product were combined and the solvent was evaporated. The residue was dissolved in isopropanol, and a solution of HCl in isopropanol was added. On addition of diisopropylethylether, the product formed an oily mass. The solvent was decanted and the remaining oil evaporated to dryness to yield 0.6 g (41%) of the title compound as a white solid.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration and evaporation of the solvent
  4. customthe crude product was purified by column chromatography on silica gel
  5. additionFractions containing the product
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in isopropanol
  8. additiona solution of HCl in isopropanol was added
  9. additionOn addition of diisopropylethylether
  10. customthe product formed an oily mass
  11. customThe solvent was decanted
  12. customthe remaining oil evaporated to dryness

Sources & evidence

ORD record
ord-a00d878eebca48a482ba3179b7d40777
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

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