Trifluoroacetic acid → 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 595932Notes

Reaction equation

COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][N:8]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][C:13]1([C:10]2[CH:11]=[CH:12][C:7]([NH2:6])=[N:8][CH:9]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cold solution of N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (100 mg, 0.29 mmol) in DCM (6 mL) was added 10 mL 30% TFA in DCM solution. The resulting solution was stirred at 0° C. for 15 min. The solvent was removed via vacuum. The resulting residue was redissolved in ethyl acetate, and the organic solution was washed with 1M NaOH, brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silicagel (ISCO) eluting with 0-100% ethyl acetate in heptane to give 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (50 mg, 0.26 mmol, 89% yield) as white color solid. LCMS (m/z): 193 (MH+), 0.35 min.

Workup

customThe solvent was removed via vacuum
dissolutionThe resulting residue was redissolved in ethyl acetate
washthe organic solution was washed with 1M NaOH, brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by flash column chromatography on silicagel (ISCO)
washeluting with 0-100% ethyl acetate in heptane

Sources & evidence

ORD record: ord-d33774b115b54df3b8b879c9c18dabfe
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

Loading…