Cesium carbonate → racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

HRID 595285Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:14][C:15]1[CH:16]=[C:17]([NH:26][C:27]2[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=2)[CH:18]=[C:19]([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)[CH:20]=1>CN(C=O)C.CCOC(C)=O>[CH:2]1([N:23]2[CH:22]=[C:21]([C:19]3[CH:18]=[C:17]([NH:26][C:27]4[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=4)[CH:16]=[C:15]([CH3:14])[CH:20]=3)[CH:25]=[N:24]2)[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromocyclohexene (0.18 mL, 1.57 mmol) and cesium carbonate (1.02 g, 3.13 mmol) were added to an oven-dried flask containing N-[3-methyl-5-(1H-pyrazol-4-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (500 mg, 1.57 mmol) dissolved in DMF (5 mL). The mixture was warmed to 80° C. and stirred overnight. The mixture was cooled to room temperature, diluted with EtOAc, and washed with 1:1 water:brine (3×). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 80% EtOAc/hexanes) to afford racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine. MS ESI calcd. for C21H21F3N5 [M+H]+ 400. found 400.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with 1:1 water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0 to 80% EtOAc/hexanes)

Sources & evidence

ORD record: ord-b6789a8b2ded4a72ab404c6fe4aa7222
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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