Hexane → HCID 66977263, compound

HRID 712202Notes

Reaction equation

HRID 712202 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1.CCCCCC>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([N:4]2[CH2:5][CH2:6][C:7]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]([CH3:1])[CH2:3]2)=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66977117HCID 66977117, compound

Product 1

HCID 66977263HCID 66977263, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3,4-dimethylpiperidine-4-carboxylate (0.2 g, 1.08 mmol) in EtOH (7 mL) was added DIPEA (0.6 mL, 3.24 mmol) at rt. The mixture was stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.21 g, 1.08 mmol) then heated up to 70° C. for 1 h. After reaction completion (by TLC), solvent was evaporated and the crude residue was purified over 100-200 M silica-gel using 10% EtOAc:hexane to obtain the desired product as a yellow solid (0.33 g, 95% yield). MS: 341.03 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ec951250b1bc41b680a14cb781224f28
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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