Hexane → Methyl 1-(5-bromopyrimidin-2-yl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylate

HRID 712293Notes

Reaction equation

HRID 712293 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:19][C:20]1[CH:21]=[N:22][C:23](Cl)=[N:24][CH:25]=1.CCCCCC>CCO>[Br:19][C:20]1[CH:21]=[N:22][C:23]([N:12]2[CH2:13][CH2:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11]2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 6066655-Bromo-2-chloropyrimidineHCID 14537079Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate

Product 1

HCID 66977205Methyl 1-(5-bromopyrimidin-2-yl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylate (0.11 g, 0.42 mmol) in EtOH (5 mL) was added 5-bromo-2-chloropyrimidine (0.09 g, 0.46 mmol) at rt and the reaction mixture heated up to 70° C. for 1 h. After completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 20% EtOAc:hexane to obtain the desired product as a yellow solid (0.09 g, 52% yield). MS: 415.17 [M+H]+.

Workup

  1. customAfter completion (by TLC), solvent was evaporated
  2. customthe crude residue purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-925083bb64b14929b652425e009fa106
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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