Potassium Carbonate → 2-(3-(Trifluoromethyl)phenyl)pyrimidin-5-amine

HRID 926764Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[C:15]([C:2]2[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 2-chloropyrimidin-5-amine (1.7 g, 13.18 mmol, 1.00 equiv) was added 3-(trifluoromethyl)phenylboronic acid (3.8 g, 20.00 mmol, 1.50 equiv), Pd(OAc)2 (0.15 g, 0.05 equiv), dppf (0.37 g, 0.05 equiv) and potassium carbonate (3.6 g, 26.09 mmol, 2.00 equiv) and the mixture was stirred overnight at 100° C. in an oil bath. The reaction was diluted with 300 mL of ethyl acetate and the solids were filtered out. The filtrate was washed with water and the organic layer dried over anhydrous sodium sulfate and then concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:15) to afford 1.2 g (38%) of 2-(3-(trifluoromethyl)phenyl)pyrimidin-5-amine as a white solid.

Workup

filtrationthe solids were filtered out
washThe filtrate was washed with water
dry with materialthe organic layer dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
washeluted with ethyl acetate/petroleum ether (1:15)

Sources & evidence

ORD record: ord-70736024776e48fb952e198898c91ffd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09289429B2

Reaction notes

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