Ammonium Chloride → 5-(4-Methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

HRID 1348551Notes

Reaction equation

HRID 1348551 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19].[CH3:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH3:20][CH:21]1[CH2:26][CH2:25][N:24]([C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[N:5]=[C:4]([CH3:11])[C:3]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 693814-MethylpiperidineHCID 230183375-Chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Product 1

HCID 230183085-(4-Methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidineYield 62.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

At room temperature, 45 mg (0.16 mmol) of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine and 63 mg (0.64 mmol) of 4-methylpiperidine were mixed. After one hour, chloroform and aqueous saturated ammonium chloride solution were added to the reaction mixture. The separated organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 35 mg (0.10 mmol, 61%) of 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

Workup

  1. washThe separated organic layer was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-35aa5fee19d247728c806d1d6912f90a
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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