Potassium Carbonate → HCID 178452147, compound

HRID 1895694Notes

Reaction equation

HRID 1895694 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-:23].[K+].[K+]>O1CCOCC1.O>[O:23]=[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71629906tert-Butyl 4-((2-chloropyrimidin-4-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 178452147HCID 178452147, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of tert-butyl 4-(2-chloropyrimidin-4-yloxy)piperidine-1-carboxylate (341.5 mg, 0.90 mmol), potassium carbonate (225.6 mg, 1.64 mmol, EMD) and 1,4-diazacyclo[2,2,2]octane (48.8 mg, 0.44 mmol, commercially available from Alfa Aesar) in dioxane/H2O (10 mL/10 mL) was heated at 70° C. for 6 h, cooled to room temperature and then evaporated. The residual was purified by flash chromatography (0 to 10% MeOH/CH2Cl2) to yield 275 mg (85%) of the product as an off-white solid.

Workup

  1. customevaporated
  2. customThe residual was purified by flash chromatography (0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-258551aca62c4cd6a8742ff85751319e
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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