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

HRID 14570

Reaction equation

Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:17][CH:18]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20][NH:19]1.[Cl-].[NH4+]>C(#N)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:19]2[CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][CH2:24][CH:18]2[CH3:17])[C:7]=1[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Into 3 ml of acetonitrile were added 0.2 g of 4,6-dichloro-5-fluoropyrimidine, 0.50 g of potassium carbonate and 0.24 g of 2,5-dimethylhexahydro-1H-azepine hydrochloride, and the mixture was stirred for 5 hours at 80° 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 0.3 g of 1-(6-chloro-5-fluoro pyrimidin-4-yl)-2,5-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-2d1e09f46e474b0085885b105c68352b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732448B2

Linked notes

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