Tetrahydrofuran → Tert-butyl 4-[(6-chloro-5-methylpyrimidin-4-yl)oxy]piperidine-1-carboxylate

HRID 1517329Notes

Reaction equation

HRID 1517329 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].[CH2:21]1[CH2:25]OC[CH2:22]1.Cl[CH:27]1[N:32](C)[C:31]([Cl:34])=CC=[N:28]1>O>[Cl:34][C:31]1[N:32]=[CH:27][N:28]=[C:25]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[C:21]=1[CH3:22]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 20073479HCID 20073479, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59566479Tert-butyl 4-[(6-chloro-5-methylpyrimidin-4-yl)oxy]piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (2.47 g, 12.3 mmol) and potassium tert-butoxide (1.42 g, 12.7 mmol) were added to a THF (20 mL) solution of 2,4-dichloro-3-methylpyrimidine (1.60 g, 9.82 mmol), and the mixture was stirred for 2 hours. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-60:40, V/V) to obtain the title compound as colorless oil (3.07 g, yield: 95%).

Workup

  1. extractionfollowed by extraction with ethyl acetate three times
  2. washThe obtained organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-60:40, V/V)

Sources & evidence

ORD record
ord-7043b3ee9c9647adbdc1131f63eb969b
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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