Ammonia → HCID 11992702, compound

HRID 421820Notes

Reaction equation

HRID 421820 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)[CH:3]=1.N.[H][H]>CO.[OH-].[Pd+2].[OH-].[C]>[N:7]1[CH:2]=[CH:3][C:4]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]2)=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 11992421HCID 11992421, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11992702HCID 11992702, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

2,2-Dimethylpropyl 4-(6-chloropyrimidin-4-yl)-1-piperazinecarboxylate (68 mg) obtained in Example 4 was dissolved in methanol (3 mL), and 0.5 ml of aqueous ammonia and a catalytic amount of palladium hydroxide-carbon were added thereto, and stirred in a hydrogen atmosphere at room temperature for 2 hours, and the reaction liquid was filtered. The filtrate was evaporated, and the resulting residue was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 20 mg of the entitled compound as an oil.

Workup

  1. customthe reaction liquid
  2. filtrationwas filtered
  3. customThe filtrate was evaporated
  4. additionthe resulting residue was diluted with ethyl acetate
  5. washwashed with water and saturated saline water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away
  8. customthe resulting residue was isolated
  9. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-29342b29a4364a27a9e619f3011ea23b
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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