Hexane → HCID 66977267, compound

HRID 712205Notes

Reaction equation

HRID 712205 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[N:29][CH:30]=1.CCCCCC>CCO>[Br:24][C:25]1[CH:26]=[N:27][C:28]([N:10]2[CH2:9][CH2:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:13]#[N:14])[CH2:12][CH2:11]2)=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 1811384-Piperidinecarbonitrile, 4-phenyl-HCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 66977267HCID 66977267, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-phenylpiperidine-4-carbonitrile (0.35 g, 1.55 mmol) in EtOH (5 mL) was added DIPEA (0.8 mL, 4.55 mmol) at rt. The mixture was stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.15 g, 1.3 mmol). The mixture was heated up to 70° C. for 1 h. After reaction completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 10% EtOAc:hexane to obtain the product as a yellow solid (0.31 g, 70% yield). MS: 343.09 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-9d670ad1c6a44e6b8ef7d31906dc4e2c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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