Lithium Hydroxide → Hydrochloric Acid

HRID 219752Notes

Reaction equation

HRID 219752 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]([CH:21]2[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]1[C:29]([C:30]([F:33])([F:32])[F:31])=[N:28][N:27]=[C:26]1[SH:34].[OH-].[Li+].[I-].[Na+]>CN(C)C=O>[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:34][C:26]3[N:25]([CH3:24])[C:29]([C:30]([F:32])([F:31])[F:33])=[N:28][N:27]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:20]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 5238Sodium IodideHCID 690261252-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidineHCID 178481704HCID 178481704, compound

Product 2

HCID 313Hydrochloric AcidHCID 690259842-tert-Butyl-4-{4-[3-(4-methyl-5-trifluoromethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclopropyl-pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
78 °C

Procedure

0.3 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidine (0.89 mmol) were dissolved in 10 ml dimethylformamide. After the addition of 0.163 g 4-Methyl-5-trifluoromethyl-4H-[1,2,4]triazole-3-thiol (0.89 mmol), 0.064 g lithium hydroxide (2.76 mmol) and 0.067 g sodium iodide (0.45 mmol), the reaction mixture was stirred at 78° C. for 3 h. After cooling, the solvent was evaporated and the residue was dissolved in 30 ml of ethyl acetate. After washing twice with water, the organic phase was dried over magnesium sulfate, filtered, and the solvent was evaporated. The residue was purified chromatography on silica gel with ethyl acetate. Fractions containing the product were combined and the solvent was evaporated. The hydrochloride was formed by addition of 4 N HCl in dioxan to yield 0.14 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  4. washAfter washing twice with water
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified chromatography on silica gel with ethyl acetate
  9. additionFractions containing the product
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0af4c1f2cb5c4731b81f62785483dac5
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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