Trimethylsilyl iodide → 4-Methyl-1-(4-trifluoromethyl-pyrimidin-2-yl)-piperidin-4-ylamine

HRID 855844Notes

Reaction equation

C(OC(=O)[NH:10][C:11]1([CH3:27])[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C>[CH3:27][C:11]1([NH2:10])[CH2:12][CH2:13][N:14]([C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4-methyl-1-(4-trifluoromethyl-pyrimidin-2-yl)-piperidin-4-yl)-carbamic acid benzyl ester (0.060 g, 0.17 mmol) in acetonitrile (1.0 mL) at room temperature was added iodotrimethysilane (0.04 mL, 0.25 mmol). The reaction mixture was stirred at 50° C. for 30 minutes, concentrated under reduced pressure and purified by flash chromatography with 3% methanol in dichloromethane to provide the titled compound. MS (CI) m/z 261(M+1)+; 1H NMR (300 MHz, methanol-d4) δ ppm 8.61(d, 1H), 6.92 (d, 1H), 4.83 (m, 2H), 4.50 (m, 2H), 3.51 (m, 2H), 1.90-1.74 (m, 4H), 1.51 (s, 3H).

Workup

concentrationconcentrated under reduced pressure
custompurified by flash chromatography with 3% methanol in dichloromethane

Sources & evidence

ORD record: ord-9e8b16d604ca4ed68640f320843b848a
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262207B2

Reaction notes

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