Hexane → Ethyl 1-[(5-bromopyrimidin-2-yl)methyl]-4-methyl-piperidine-4-carboxylate

HRID 712232Notes

Reaction equation

HRID 712232 reaction equation
Cl.[CH3:2][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27]([CH2:30]Br)=[N:28][CH:29]=1.CCCCCC>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([CH2:30][N:6]2[CH2:7][CH2:8][C:3]([CH3:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 19361804Ethyl 4-methylpiperidine-4-carboxylate hydrochlorideHCID 205577975-Bromo-2-(bromomethyl)pyrimidine

Product 1

HCID 66977105Ethyl 1-[(5-bromopyrimidin-2-yl)methyl]-4-methyl-piperidine-4-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-methylpiperidine-4-carboxylate hydrochloride (0.08 g, 0.48 mmol) in EtOH (5.0 mL) was added DIPEA (0.22 mL, 1.20 mmol) at rt and the mixture stirred at rt for 10 minutes followed by addition of 5-bromo-2-(bromomethyl)pyrimidine (0.10 g, 0.40 mmol). The reaction was heated up to 70° C. for 1 h. After completion of reaction (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 (0.10 g, 73% yield). 1H NMR (DMSO-d6): δ 1.09 (s, 3H), 1.13 (t, J=7.20 Hz, 3H), 1.45 (m, 2H), 2.00 (m, 2H), 3.12 (m, 2H), 3.32 (m, 2H), 3.62 (q, J=7.20 Hz, 2H), 4.08 (m, 2H) and 8.94 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-f37c94cc85d34678b1799566141daa7f
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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