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

HRID 14574

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][C@H:17]1[CH2:23][CH2:22][CH2:21][C@H:20]([CH3:24])[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][C@@H:20]([CH3:24])[CH2:21][CH2:22][CH2:23][C@@H:17]2[CH3:16])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Into 3 ml of acetonitrile were added 0.2 g of 4,6-dichloropyrimidine, 0.56 g of potassium carbonate and 0.31 g of trans-2,6-dimethylhexahydro-1H-azepine hydrochloride, and the mixture was stirred for 2 hours at 60° C. 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 0.30 g of 1-(6-chloropyrimidin-4-yl)-trans-2,6-dimethylhexahydro-1H-azepine.

Workup

temperatureThe reaction mixture was cooled to near room temperature
extractionthe mixture was extracted with tert-butyl methyl ether three times
washThe organic layers were washed with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b9487ef63e354ac99b603e23139642a2
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732448B2

Linked notes

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