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

HRID 1626350Notes

Reaction equation

HRID 1626350 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[Cl:21][C:22]1[C:27]([CH3:28])=[C:26](Cl)[N:25]=[CH:24][N:23]=1>C1COCC1>[Cl:21][C:22]1[N:23]=[CH:24][N:25]=[C:26]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[C:27]=1[CH3:28]

Participants

5

Reactant 3

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 8188604,6-Dichloro-5-methylpyrimidineHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Potassium tert-butoxide (3.4 gm, 0.0306 moles) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (6.8 gm, 0.0368 moles) and 4,6-dichloro-5-methylpyrimidine (5.0 gm, 0.0368 moles) in dry THF at 0° C. and the reaction mixture was stirred for 15-20 hours at 30° C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to collect 5.1 gm off-white solid product.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto collect 5.1 gm off-white solid product

Sources & evidence

ORD record
ord-7023c5c9dbe849e18db40158d70a49d0
Source dataset
uspto-grants-2014_07
Patent number
US08785463B2

Reaction notes

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