Potassium Carbonate → 1-(6-chloropyrimidin-4-yl)-2,5-dimethylhexahydro-1H-azepine

HRID 14569

Reaction equation

HRID 14569 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:16][CH:17]1[CH2:23][CH2:22][CH:21]([CH3:24])[CH2:20][CH2:19][NH:18]1.[Cl-].[NH4+]>C(#N)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:18]2[CH2:19][CH2:20][CH:21]([CH3:24])[CH2:22][CH2:23][CH:17]2[CH3:16])[CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 665948322,5-dimethylhexahydro-1H-azepine hydrochloride

Product 1

HCID 593411511-(6-chloropyrimidin-4-yl)-2,5-dimethylhexahydro-1H-azepineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into 3 ml of acetonitrile were added 0.2 g of 4,6-dichloropyrimidine, 0.56 g of potassium carbonate and 0.26 g of 2,5-dimethylhexahydro-1H-azepine hydrochloride, and the mixture was stirred for 3 hours at 80%. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.3 g of 1-(6-chloropyrimidin-4-yl)-2,5-dimethylhexahydro-1H-azepine.

Workup

  1. extractionthe mixture was extracted with tert-butyl methyl ether three times
  2. washThe organic layers were washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-905bb21b8073490a8c890645dc09df44
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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