Potassium tert-butoxide → HCID 86677565, compound

HRID 2401108Notes

Reaction equation

HRID 2401108 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][CH2:20][NH:21][C:22]2[CH:23]=[N:24][C:25]([Cl:28])=[N:26][CH:27]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O)C.CC(C)([O-])C.[K+]>O1CCCC1>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[N:21]([C:22]3[CH:27]=[N:26][C:25]([Cl:28])=[N:24][CH:23]=3)[CH2:20][CH2:19]2)[CH2:7][CH2:8]1)=[O:13])([CH3:17])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86677564HCID 86677564, compound

Product 1

HCID 86677565HCID 86677565, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[2-(2-chloro-pyrimidin-5-ylamino)-ethyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (188 mg, 0.46 mmol) in tetrahydrofuran (4 mL) was added 1 M solution of potassium-tert-butoxide in tetrahydrofuran (0.55 mL, 0.55 mmol). The resulting mixture was stirred for 2 hours at ambient temperature and then added NaHCO3 (aq) (20 mL), extracted with EtOAc (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford a crude solid which was then purified by flash column chromatography (0 to 10% MeOH/CH2Cl2) to provide 125 mg (74% yield) of the title compound as a solid.

Workup

  1. extractionadded NaHCO3 (aq) (20 mL), extracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a crude solid which
  6. customwas then purified by flash column chromatography (0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4adaf9228fa64ca4a3bdd00ebecd72a5
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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