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

HRID 219748Notes

Reaction equation

HRID 219748 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)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[C:30]([C:31]([F:34])([F:33])[F:32])=[N:29][N:28]=[C:27]1[SH:35].[I-].[K+].O>CN(C)C=O.C(OCC)(=O)C>[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:35][C:27]3[N:26]([CH3:25])[C:30]([C:31]([F:33])([F:32])[F:34])=[N:29][N:28]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 666731042-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidineHCID 178481704HCID 178481704, compound

Product 1

HCID 115405562-tert-Butyl-4-{4-[3-(4-methyl-5-trifluoromethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclobutyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.4 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (1.14 mmol), 0.22 g of 4-methyl-5-trifluoromethyl-4H-[1,2,4]triazole-3-thiol (1.2 mmol), 0.07 g of lithium-hydroxide (2.92 mmol) and a spatula tip of potassium iodide were stirred in 10 ml of dimethylformamide for 14 h at room temperature and for an additional 2 h at 80° C. After addition of water and ethyl acetate, the organic layer was separated, dried over magnesium sulfate, filtered and the solvent was evaporated. The residue was purified twice by column chromatography on silica gel using dichloromethane-methanol (1-5%). Fractions containing the product were combined, the solvents evaporated, the residue stirred with acetonitrile yielding 0.03 g (5.3%) of the product as a solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified twice by column chromatography on silica gel
  6. additionFractions containing the product
  7. customthe solvents evaporated

Sources & evidence

ORD record
ord-d2f2f04094374ae9ae7469d88d01b685
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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