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

HRID 896222Notes

Reaction equation

HRID 896222 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[CH:30]=[N:29][N:28]=[C:27]1[SH:31].[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:31][C:27]3[N:26]([CH3:25])[CH:30]=[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 178481306HCID 178481306, compound

Product 1

HCID 223498702-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-tert-butyl-pyrimidine hydrochlorideYield 83%

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), 0.35 g of 4-Methyl-4H-[1,2,4]triazole-3-thiol (3.04 mmol), 0.2 g of lithium-hydroxide (8.35 mmol) and a spatula tip of potassium iodide werde stirred for 72 h in 20 ml of dimethylformamide. Water and ethyl acetate were added and the organic layer was separated, dried over magnesium sulfate, filtered and the solvent was evaporated. The resdue was subjected to a column chromatography on silica gel using dichloromethane-methanol(2-10%). Fractions containing the product were combined, the solvent was evaporated and the residue re-dissolved in isopropanol. The solution was treated with HCl/isopropanol. Diisopropylethylether was added whereby an oily precipitate formed. The solvent was decanted and the remaining oil evaporated to dryness to yield 1.1 g (77%) of the title compound as a white solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. additionFractions containing the product
  6. customthe solvent was evaporated
  7. dissolutionthe residue re-dissolved in isopropanol
  8. additionThe solution was treated with HCl/isopropanol
  9. additionDiisopropylethylether was added whereby an oily precipitate
  10. customformed
  11. customThe solvent was decanted
  12. customthe remaining oil evaporated to dryness

Sources & evidence

ORD record
ord-fb00fcc9cab5429085e2b16283fd38fa
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

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