Diisopropylethylamine → Methyl 1-(5-bromopyrimidin-2-yl)-4-hydroxy-3-methyl-piperidine-3-carboxylate

HRID 712201Notes

Reaction equation

HRID 712201 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][C:4]1([CH3:13])[C:9]([O:11][CH3:12])=[O:10].CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([N:6]2[CH2:7][CH2:8][CH:3]([OH:2])[C:4]([CH3:13])([C:9]([O:11][CH3:12])=[O:10])[CH2:5]2)=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66976939Methyl 4-hydroxy-3-methyl-piperidine-3-carboxylate hydrochloride

Product 1

HCID 66976854Methyl 1-(5-bromopyrimidin-2-yl)-4-hydroxy-3-methyl-piperidine-3-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-hydroxy-3-methyl-piperidine-3-carboxylate hydrochloride (0.4 g, 1.91 mmol) in EtOH (10 mL) was added DIPEA (1.7 mL, 9.55 mmol) at rt. The resulted mixture was stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.37 g, 1.91 mmol). The reaction mixture was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue was purified over 100-200 M silica-gel by using 25% EtOAc: hexane to obtain the product as an off white solid (0.345 g, 55%). MS: 330.12 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated up to 70° C. for 1 h
  2. customAfter completion of reaction (by TLC), solvent
  3. customwas evaporated
  4. customthe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-502703663f3542f98608486d8ee87573
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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