3-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine → 2-{2-[Methyl(pyridin-3-yl)amino]pyridin-3-yl}-1,1-dipyridin-3-ylethanol

HRID 1686073Notes

Reaction equation

HRID 1686073 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:8][C:9]2[C:10]([N:15]([CH3:22])[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=1.CC(C)([O-:32])C.[K+]>CS(C)=O.CC(O)(C)C>[CH3:22][N:15]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[C:9]([CH2:8][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[OH:32])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 166623133-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 578678002-{2-[Methyl(pyridin-3-yl)amino]pyridin-3-yl}-1,1-dipyridin-3-ylethanolYield 73.3%

Reagents, catalysts & solvents 1

HCID 86634320DMSO t-BuOHSolvent

Procedure

To a solution of 3-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine (34 mg) in 1.2 mL of DMSO:t-BuOH (80:20) was added potassium tert-butoxide (21 mg). The reaction was stirred under an oxygen balloon at room temperature for 2 h, then quenched by adding 2 drops of water. Purification by reverse phase HPLC gave 26 mg of 2-{2-[methyl(pyridin-3-yl)amino]pyridin-3-yl}-1,1-dipyridin-3-ylethanol as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.54 (d, J=1.9 Hz, 2H), 8.47 (dd, J=4.6, 1.7 Hz, 2H), 8.35 (dd, J=4.6, 1.7 Hz, 1H), 8.21 (dd, J=4.6, 1.2 Hz, 1H), 8.05 (d, J=2.7 Hz, 1H), 7.59-7.57 (m, 2H), 7.24-7.15 (m, 4H), 7.08-7.05 (m, 1H), 6.99-6.95 (m, 1H), 4.57 (s, 1H), 3.55 (s, 2H), 3.21 (s, 3H).

Workup

  1. customquenched
  2. additionby adding 2 drops of water
  3. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-1a0a0a198a25432c82e9570c2c1de03b
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

Loading…